A kind of preparation method of benzothiazine derivative
A technology of benzothiazine and derivatives, which is applied in the field of preparation of benzothiazine derivatives, can solve the problem of metal residues, high cost, difficult preparation of 2-iodo-N-(2-iodoethyl)aniline raw materials, etc. question
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[0023] The embodiment of the present invention discloses a preparation method of benzothiazine derivatives, comprising:
[0024] Reaction of the aryl ortho-halogenated enaminoketone shown in formula (I) with a sulfur source in a solvent to obtain a benzothiazine derivative;
[0025]
[0026] Among them, R 1 C1-C5 alkyl, C1-C5 alkoxy, nitro, Cl or F;
[0027] R 2 with R 3 independently selected from hydrogen or C1-C5 alkyl groups;
[0028] X is I or Br.
[0029] In the process of preparing benzothiazine derivatives, the present invention uses aryl ortho-halogenated enaminones and sulfur sources as raw materials, the raw materials are simple and easy to obtain, the reaction conditions are mild, the environment is friendly, and transition metal catalysts are not required to produce The rate is higher.
[0030] In the process of preparing benzothiazine derivatives, the aryl ring ortho-haloenaminoketone is preferably 3-(2-iodophenylamino)-5,5-dimethylcyclo-2-enone , 3-(2-...
Embodiment 1
[0041] Example 1 Preparation of 2,2-dimethyl-2,3-dihydro-1H-phenothiazin-4(10H)-one with structure of formula (II)
[0042]
[0043]Add 3-(2-iodophenylamino)-5,5-dimethylcyclo-2-enone or 3-(2-bromophenylamino)-5,5-dimethylcyclo -2-enone 0.5mmol, potassium sulfide 0.6mmol, react in DMF solvent at 130°C for 12h under the protection of argon, and TLC detects that the reaction is complete; Wash column chromatography, obtain 2,2-dimethyl-2,3-dihydro-1H-phenothiazin-4(10H)-ketone light yellow solid with formula (II) structure, its yield rate is 80 %, the melting point is 254.4-255.7°C.
[0044] Detect the above compound prepared, and the detection results are as follows:
[0045] Infrared spectrum (neat, ν, cm-1): 3247, 2955, 2927, 1611, 1522, 1468, 1306, 746;
[0046] Proton NMR spectrum (400MHz, DMSO) δ8.85 (s, 1H, N-H), 6.86 (t, J=5.8Hz, 1H, Ar-H), 6.78-6.67 (m, 2H, Ar-H), 6.54 (d, J=7.6Hz, 1H, Ar-H), 2.20(s, 2H, -CH 2 ), 2.15(s, 2H, -CH 2 ), 1.00 (s, 6H, -CH 3 );
[0...
Embodiment 2
[0049] Example 2 Preparation of 2,2,7-trimethyl-2,3-dihydro-1H-phenothiazin-4(10H)-one with structure of formula (Ⅲ)
[0050]
[0051] Add 3-(2-iodo-4-methylphenylamino)-5,5-dimethylcyclo-2-enone or 3-(2-bromo-4-methylphenylamino) into a 10mL reaction tube )-5,5-dimethylcyclo-2-enone 0.5mmol, potassium sulfide 0.6mmol, reacted at 130°C for 12h in a DMF solvent under the protection of argon, and the reaction was complete by TLC; after the reaction, the solvent was removed under reduced pressure , using ethyl acetate and petroleum ether as eluent column chromatography to obtain 2,2,7-trimethyl-2,3-dihydro-1H-phenothiazin-4(10H)-one orange solid, which The yield was 95%, and the melting point was 283.3-285.6°C.
[0052] Detect the above compound prepared, and the detection results are as follows:
[0053] Infrared spectrum (neat, ν, cm-1): 3245, 2956, 2921, 1592, 1560, 1478, 1310, 814, 746;
[0054] Proton NMR spectrum (400MHz, DMSO) δ8.80(s, 1H, N-H), 6.66(d, J=7.8Hz, 1H, ...
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