2-Ethyl-3-(3,5-dichlorophenylcarbamoyl) thiazolidine-2-carboxylic acid methyl ester → 7a-Ethyl-6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole-5,7-dion

HRID 903890Notes

Reaction equation

C[O:2][C:3]([C:5]1([CH2:21][CH3:22])[N:9]([C:10](=[O:20])[NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)[CH2:8][CH2:7][S:6]1)=O>C[O-].[Na+].CO>[CH2:21]([C:5]12[C:3](=[O:2])[N:11]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=3)[C:10](=[O:20])[N:9]1[CH2:8][CH2:7][S:6]2)[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

0.70 g of 2-ethyl-3-(3,5-dichlorophenylcarbamoyl)thiazolidine-2-carboxylic acid methyl ester was added to 20 ml of 0.1 N sodium methylate-methanol solution, heated at 50° C. for 20 minutes. The reaction mixture was cooled and filtered. The resulting filtrate was 0.16 g (yield 25%) of 7a-ethyl-6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole-5,7-dion (compound No. 7). The results of elementary analysis and a melting point were given in table 1.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered

Sources & evidence

ORD record: ord-0a471cf24cf248e793974a089fba4f27
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04229461

Reaction notes

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