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Synthetic method of 2-amino-4-aryl-5-methylthiothiazole compounds

A technology of methylthiothiazole and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of poisonous and harmful use, low yield and high cost, and achieve the effects of mild reaction conditions, short process lines and low cost

Active Publication Date: 2022-06-10
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the above method can be used to prepare 2-amino-4-aryl-5-methylthiothiazole compounds, there are many shortcomings: the raw materials used in the synthesis process are not easy to obtain, and the cost is high; the use of toxic and harmful organic solvents, Or the yield is low, or the post-processing is cumbersome, etc.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: Synthesis of 2-amino-4- (p-nitrophenyl) -5-methylthiothiazole

[0018] (a) Weigh p-nitroacetophenone (6.52g, 39.5mmol), dissolve in a round-bottom flask added to a mixture of 40% hydrobromide (20ml) and dimethyl sulfoxide (20ml), sealed, protected from light, heating the mixture to 40 ° C, reaction for 10 hours, cooling. Ether (20ml) and isopropanol (20ml) were added to the round-bottom flask, refrigerated overnight, a large amount of precipitate was precipitated, filtered, washed with dichloromethane, dried to α-bromo-p-nitroacetophenone dimethyl sulfonium salt, white crystals, weighed to 12.16g, yield 80%, melting point 119-123 °C.

[0019](b) Weigh the sulfonium salt (0.5 g, 1.3 mmol) prepared in the above steps, add water (5 ml) to dissolve, add thiourea (0.1 g, 1.3 mmol), stir at room temperature for 3 hours, then add ethanol (5 ml), heat up to 90 °C for 12 h. Cooled in an ice water bath, refrigerated overnight, precipitated, filtered, washed with cold ethyl...

Embodiment 2

[0020] Example 2: Synthesis of 2-amino-4-(p-chlorophenyl)-5-methylthiothiazole

[0021] (a) Weigh p-chloroacetophenone (6.11g, 39.5mmol) in a round-bottom flask, add dimethyl sulfoxide (10ml) and hydrobromide (20ml), sealed, protected from light, the mixture was heated to 60 ° C, reaction for 8 hours, cooled. Ether (20ml) and isopropanol (20ml) were added to the round-bottom flask, refrigerated and left overnight, a large amount of precipitate was precipitated, filtered, washed with dichloromethane, naturally dried to α-bromo-p-chloroacetophenone dimethyl sulfonium salt, white crystals, weighed to 10.35g, yield 70%, melting point 124-128 ° C.

[0022] (b) Weigh the sulfonium salt (0.50 g, 1.3 mmol) obtained in step (a), add water (10 ml) to dissolve, add thiourea (0.2 g, 2.6 mmol), stir at room temperature for 3 hours, add ethanol (5 ml), heat up to 70 °C for 10 h. Cooled, left in refrigeration overnight, precipitation without sediment, dichloromethane extraction, washed, saturate...

Embodiment 3

[0023]Example 3: Synthesis of 2-amino-4-(p-fluorophenyl)-5-methylthiothiazole

[0024] (a) Weigh p-fluoroacetophenone (5.45g, 39.5 mmol), dissolved in a round bottom flask added with a mixture of 40% hydrobromide (20 ml) and dimethyl sulfoxide (20 ml), sealed, protected from light, the mixture was heated to 30 ° C, the reaction for 12 hours, cooled. Ether (20ml) and isopropanol (20ml) were added to the round-bottom flask, refrigerated and left overnight, precipitate, filtered, washed with dichloromethane, dried, to give α-bromo-p-fluoroacetophenone dimethyl sulfonium salt, white crystals, weighed to 8.49g, yield 60%, melting point 120-124 °C.

[0025] (b) weighing and weighing step (a) to obtain α- bromo p-fluoroacetophenone dimethyl sulfonium salt (0.50g, 1.4mmol), add water (10ml) dissolved, add thiourea (0.55g, 7.2mmol), stirred at room temperature for 3 hours, then added ethanol (5ml), heated to 60 ° C reaction for 14 hours. Cooled, refrigerated overnight, precipitation withou...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and relates to a method for efficiently and conveniently synthesizing 2-amino-4-aryl-5-methylthiothiazole compounds. It comprises the following synthetic steps: (1) arylethanone is dissolved in DMSO / HBr mixed system, and heating reaction makes α-bromoacetophenonyl dimethyl sulfonium salt; (2) in step (1) The obtained sulfonium salt is dissolved in water, thiourea is added, and stirred at room temperature; then ethanol is added, and the heating reaction is continued to obtain 2-amino-4-aryl-5-methylthiothiazole.

Description

Technical field [0001] The present invention belongs to the field of organic chemical synthesis technology, relates to an efficient and simple synthesis of 2-amino-4-aryl-5-methylthiothiazole compound method. Specifically, it involves the synthesis method of compounds of formula I. [0002] [0003] where: R is NO 2 , F, Cl, or CH 3 。 Background [0004] Thiothiazole compounds are a class of heterocyclic compounds with a variety of biological activities and pharmacological activities such as anti-cancer, analgesic and anti-inflammatory, antibacterial and antiviral. Iriuchijima et al. disclosed the reaction of 2-methylsulfonyl-1-acetophenone with thiourea as raw material to synthesize 2-amino-4-phenyl-5-methylthiothiazole (Iriuchijima S, Hasegawa K, JP 7777061, (1975); Chem. Abstr., (1977) 87, 201513), studies have shown that the compound has important biological and pharmacological activities such as bactericidal, antiviral and cytotoxic activities. Chinese Patent CN20091004883...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/54
CPCC07D277/54
Inventor 曹志凌吴巧陈静朱丹丹马晓冬滕文琪宋晓凯刘玮炜史大华陶传洲赵跃强唐丽娟王建殷龙朱荟龙
Owner HUAIHAI INST OF TECH
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