2-Aminothiazole → 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide1,1-dioxide

HRID 28003Notes

Reaction equation

HRID 28003 reaction equation
[C:1]([C:5]1[N:6]([CH3:17])[S:7](=[O:16])(=[O:15])[C:8]2[CH:14]=[CH:13][S:12][C:9]=2[C:10]=1[OH:11])([O:3]C)=O.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[S:12][CH:13]=[CH:14][C:8]=2[S:7](=[O:16])(=[O:15])[N:6]([CH3:17])[C:5]=1[C:1]([NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[O:3]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 546905992H-Thieno(2,3-e)-1,2-thiazine-3-carboxylic acid, 4-hydroxy-2-methyl-, methyl ester, 1,1-dioxide

Product 1

HCID 547213384-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.9 G. of 3-carbomethoxy-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide are suspended together with 0.9 g. of 2-aminothiazole in 250 ml. of absolute xylene and heated to reflux for 7 hours, by which means 150 ml. of xylene are slowly distilled off. The residual xylene is then evaporated in vacuo. The crystalline residue is recrystallized from ethanol. There is obtained 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of melting point 217° C. (decomposition).

Workup

  1. temperatureto reflux for 7 hours, by which
  2. distillationof xylene are slowly distilled off
  3. customThe residual xylene is then evaporated in vacuo
  4. customThe crystalline residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-47b5c00db0fb47449dc10e10155d809e
Source dataset
uspto-grants-1980_09
Patent number
US04224445

Reaction notes

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