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Preparation method for (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione

A phenylthiazole and imidazo technology, applied in the field of organic synthesis, can solve problems such as harsh conditions and excessively long reaction time, and achieve the effects of simple operation, shortening reaction time and improving reaction yield

Inactive Publication Date: 2011-04-13
安徽泰格生物技术股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction time of the method is still too long, the conditions are harsh, and the two-step total yield is 68%, which fails to fundamentally solve the above problems

Method used

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  • Preparation method for (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione
  • Preparation method for (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione
  • Preparation method for (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Dissolve 50g of tetrahydro-(4R)-carboxy-(2s)-phenylthiazole (0.24mol) and 67mL of benzyl isocyanate (0.54mol) in a mixed solution of 500mL of glacial acetic acid and acetic anhydride (molar ratio 20:1 ) in a water bath at 90°C for 3 hours; after the reaction, the solvent was removed under reduced pressure, the residue was dissolved in 250ml of anhydrous methanol, and frozen and crystallized at 0°C to obtain 71g of white solid (7aR)-3-phenyl-6-benzyl -1H,3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione (0.22mol, yield 93%), melting point 79-80°C.

[0029] 1 HNMR (CDCl 3 ), δ: 7.30-7.45(m, 10H), 6.41(s, 1H), 4.67(s, 2H), 4.52(t, 1H), 3.30(dd, 1H), 3.15(dd, 1H); elemental analysis C 18 h 16 N 2 o 2 S (324.4) measured value (theoretical value), %: (C)=66.41 (66.58), (H)=4.91 (4.93), (N)=8.71 (8.63), (S)=9.95 (9.86).

Embodiment 2

[0031] Dissolve 50g of tetrahydro-(4R)-carboxy-(2s)-phenylthiazole (0.24mol) and 67mL of benzyl isocyanate (0.54mol) in a mixed solution of 500mL of glacial acetic acid and acetic anhydride (molar ratio 20:1 ), refluxed in a water bath at 90°C for 6h; after the reaction, the solvent was removed under reduced pressure, and the residual substance was dissolved in 250ml of anhydrous methanol, and frozen and crystallized at 0°C to obtain 72.1g of white solid (7aR)-3-phenyl-6-benzyl -1H,3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione (0.22mol, yield 94.4%), melting point 79-80°C.

[0032] 1 HNMR (CDCl 3 ), δ: 7.30-7.45(m, 10H), 6.41(s, 1H), 4.67(s, 2H), 4.52(t, 1H), 3.30(dd, 1H), 3.15(dd, 1H); elemental analysis C 18 h 16 N 2 0 2 S (324.4) measured value (theoretical value), %: (C)=66.41 (66.58), (H)=4.91 (4.93), (N)=8.71 (8.63), (S)=9.95 (9.86).

Embodiment 3

[0034] Dissolve 50g of tetrahydro-(4R)-carboxy-(2s)-phenylthiazole (0.24mol) and 89mL of benzyl isocyanate (0.72mol) in a mixed solution of 500mL of glacial acetic acid and acetic anhydride (molar ratio 20:1 ) in a water bath at 90°C for 3 hours; after the reaction, the solvent was removed under reduced pressure, the residue was dissolved in 250ml of anhydrous methanol, and frozen and crystallized at 0°C to obtain 72.4g of white solid (7aR)-3-phenyl-6- Benzyl-1H,3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione (0.23mol, yield 94.8%), melting point 79-80°C.

[0035] 1 HNMR (CDCl 3 ), δ: 7.30-7.45(m, 10H), 6.41(s, 1H), 4.67(s, 2H), 4.52(t, 1H), 3.30(dd, 1H), 3.15(dd, 1H); elemental analysis C 18 h 16 N 2 o 2 S (324.4) measured value (theoretical value), %: (C)=66.41 (66.58), (H)=4.91 (4.93), (N)=8.71 (8.63), (S)=9.95 (9.86).

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Abstract

The invention provides a preparation method for (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione. The method is as follows: benzyl isocyanate is taken as a ring-closing agent to be subject to one-step circularization synthesis with tetrahydro-(4R)-carboxy-(2s)-phenyl thiazole to obtain the (7aR)-3-phenyl-6-benzyl-1H,3H-imidazo [1,5-C] thiazole-(6H,7aH) 5,7-dione. The method provided by the invention has the following advantages: (1) the benzyl isocyanate is taken as the ring-closing agent to be subject to one-step reaction to obtain the product, so that the operation is simple, the reaction flow is simplified, and the response time is shorten; and (2) the reaction yield is improved and can be up to more than 93%.

Description

technical field [0001] The present invention relates to a method for preparing (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione, which belongs to the field of organic synthesis. Background technique [0002] (7aR)-3-Phenyl-6-benzyl-1H,3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione is an important intermediate in the synthesis of d-biotin , the basic skeleton of the three-dimensional structure of biotin can be obtained after the intermediate is opened, introduced side chains, and cyclized. [0003] Currently, the method for preparing (7aR)-3-phenyl-6-benzyl-1H,3H-imidazo[1,5-C]thiazole-(6H,7aH)5,7-dione (I) is usually Using sodium isocyanate or sodium cyanate as a ring-closing reagent, carry out a ring-closure reaction with tetrahydro-(4R)-carboxy-(2s)-phenylthiazole (II) to obtain (7aR)-3-phenyl- 1H, 3H-imidazo[1,5-C]thiazole-(6,7aH)-5,7-dione (III), and then prepared by reacting with benzyl bromide. However, the existing methods have long reaction ti...

Claims

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Application Information

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IPC IPC(8): C07D513/04
Inventor 孙林
Owner 安徽泰格生物技术股份有限公司