2-Aminothiazole → 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[3,4-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

HRID 28012Notes

Reaction equation

HRID 28012 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][S:9][CH:10]=[C:6]2[S:5](=[O:12])(=[O:11])[N:4]([CH3:13])[C:3]=1[C:14]([O:16]C)=O.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:7]2=[CH:8][S:9][CH:10]=[C:6]2[S:5](=[O:11])(=[O:12])[N:4]([CH3:13])[C:3]=1[C:14]([NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[O:16]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 547194904-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide

Product 1

HCID 546941094-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[3,4-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.9 G. of 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide are suspended together with 0.4 g. of 2-aminothiazole in 100 ml. of absolute xylene and heated to reflux for 4 hours, 70 ml. of xylene being slowly distilled off. A crystalline precipitate separates from the cooled solution and is filtered off under suction. There is obtained 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[3,4-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of melting point 243°-245° C. (decomposition).

Workup

  1. temperatureto reflux for 4 hours
  2. distillationof xylene being slowly distilled off
  3. filtrationA crystalline precipitate separates from the cooled solution and is filtered off under suction

Sources & evidence

ORD record
ord-e8a76991d2d5482f9586fd5bae488745
Source dataset
uspto-grants-1980_09
Patent number
US04224445

Reaction notes

Loading…