Preparation method of 2, 2'-azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salt

Abstract

The invention discloses a preparation method of a 2, 2'-azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salt. The raw materials used in the preparation method are easily available, and the price islow, the production cost can be greatly reduced while ensuring a high reaction yield, so that enlarged production is facilitated, meanwhile, the preparation method is different from the previous new preparation process, and the new preparation process is beneficial to academic research, industrial research and practice of ABTS in the field, so that the development of related technologies and related industrial economy in the field is promoted.

Description

technical field

[0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 2,2'-azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salt. Background technique

[0002] 2,2′-Azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salts, in particular, 2,2′-Azino-bis(3-ethylbenzothiazoline-6- Sulfonic acid) diamine salt (ABTS) can be used in biochemical research, for example, the spectral reagent of free chlorine, the chromogenic substrate of enzyme-linked immunosorbent assay, the substrate of peroxidase, used in ELISA experiment. At present, there are few literature reports on the synthesis of 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS), and the price of ABTS is relatively expensive. New optimization of ABTS is sought The synthetic method is of great significance. In the prior art, Chinese patent 1 (application number CN201811052610.0) discloses a synthesis method of 2,2'-hydrazine-bis(3-ethylbenzothiazoli...

Examples

Embodiment 1

[0035] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0036] step 1:

[0037]

[0038] In a reactor, compound 2 was prepared by reacting 1 mole of compound 1 with diethyl sulfate. Wherein, the molar ratio of compound 1 to diethyl sulfate is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0039] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 65%.

[0040] Step 2:

[0041]

[0042] Compound 3 was prepared by reacting 1 mole of compound 2 with carbon disulfide in a reactor. Among them, the molar ratio of compound 2 to carbon disulfide is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 60° C., ...

Embodiment 2

[0063] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0064] step 1:

[0065]

[0066] Compound 2 was prepared by reacting 1 mole of compound 1 with ethyl bromide in a reactor. Wherein, the molar ratio of compound 1 to bromoethane is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0067] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 60%.

[0068] Step 2:

[0069]

[0070] In a reactor, compound 3 is prepared by reacting 1 mole of compound 2, a halogenating agent (bromine) and carbon disulfide. Wherein, the molar ratio of compound 2 to the halogenation reagent is 1:1, the molar ratio of compound 2 to carbon...

Embodiment 3

[0091] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0092] step 1:

[0093]

[0094] Compound 2 was prepared by reacting 1 mole of compound 1 with ethyl bromide in a reactor. Wherein, the molar ratio of compound 1 to bromoethane is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0095] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 62%.

[0096] Step 2:

[0097]

[0098] In a reactor, compound 3 is prepared by reacting 1 mole of compound 2, a halogenating agent (bromine) and carbon disulfide. Wherein, the molar ratio of compound 2 to the halogenation reagent is 1:1, the molar ratio of compound 2 to carbon...

technical field

[0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 2,2'-azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salt. Background technique

[0002] 2,2′-Azino-bis(3-alkylbenzothiazoline-6-sulfonic acid) salts, in particular, 2,2′-Azino-bis(3-ethylbenzothiazoline-6- Sulfonic acid) diamine salt (ABTS) can be used in biochemical research, for example, the spectral reagent of free chlorine, the chromogenic substrate of enzyme-linked immunosorbent assay, the substrate of peroxidase, used in ELISA experiment. At present, there are few literature reports on the synthesis of 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS), and the price of ABTS is relatively expensive. New optimization of ABTS is sought The synthetic method is of great significance. In the prior art, Chinese patent 1 (application number CN201811052610.0) discloses a synthesis method of 2,2'-hydrazine-bis(3-ethylbenzothiazoli...

Examples

Embodiment 1

[0035] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0036] step 1:

[0037]

[0038] In a reactor, compound 2 was prepared by reacting 1 mole of compound 1 with diethyl sulfate. Wherein, the molar ratio of compound 1 to diethyl sulfate is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0039] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 65%.

[0040] Step 2:

[0041]

[0042] Compound 3 was prepared by reacting 1 mole of compound 2 with carbon disulfide in a reactor. Among them, the molar ratio of compound 2 to carbon disulfide is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 60° C., ...

Embodiment 2

[0063] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0064] step 1:

[0065]

[0066] Compound 2 was prepared by reacting 1 mole of compound 1 with ethyl bromide in a reactor. Wherein, the molar ratio of compound 1 to bromoethane is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0067] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 60%.

[0068] Step 2:

[0069]

[0070] In a reactor, compound 3 is prepared by reacting 1 mole of compound 2, a halogenating agent (bromine) and carbon disulfide. Wherein, the molar ratio of compound 2 to the halogenation reagent is 1:1, the molar ratio of compound 2 to carbon...

Embodiment 3

[0091] This example provides a preparation and purification process of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS):

[0092] step 1:

[0093]

[0094] Compound 2 was prepared by reacting 1 mole of compound 1 with ethyl bromide in a reactor. Wherein, the molar ratio of compound 1 to bromoethane is 1:1; the solvent is tetrahydrofuran, the reaction temperature is 20° C., the reaction pressure is normal pressure, the reaction time is 8 hours, and the reaction is completed.

[0095] The solvent was spun off, ethyl acetate was added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate was spun off to obtain compound 2 with a yield of 62%.

[0096] Step 2:

[0097]

[0098] In a reactor, compound 3 is prepared by reacting 1 mole of compound 2, a halogenating agent (bromine) and carbon disulfide. Wherein, the molar ratio of compound 2 to the halogenation reagent is 1:1, the molar ratio of compound 2 to carbon...

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