2-Aminothiazole → 3,4-dihydro-2-methyl-3-oxo-4-(2-thiazolyl-carbamoyl)-2 H-thieno[2,3-e]1,2-thiazine 1,1-dioxide

HRID 372264Notes

Reaction equation

HRID 372264 reaction equation
CO[C:3]([CH:5]1[C:10]2[S:11][CH:12]=[CH:13][C:9]=2[S:8](=[O:15])(=[O:14])[N:7]([CH3:16])[C:6]1=[O:17])=[O:4].[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>C1(C)C(C)=CC=CC=1>[CH3:16][N:7]1[C:6](=[O:17])[CH:5]([C:3](=[O:4])[NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[C:10]2[S:11][CH:12]=[CH:13][C:9]=2[S:8]1(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 166399353,4-dihydro-4-methoxycarbonyl-2-methyl-3-oxo-2H-thieno[2,3-e] 1,2-thiazine 1,1-dioxide

Product 1

HCID 166399413,4-dihydro-2-methyl-3-oxo-4-(2-thiazolyl-carbamoyl)-2 H-thieno[2,3-e]1,2-thiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.15 G. of 3,4-dihydro-4-methoxycarbonyl-2-methyl-3-oxo-2H-thieno[ 2,3-e] 1,2-thiazine 1,1-dioxide and 0.071 g. of 2-aminothiazole are dissolved in 30 ml. of absolute xylene and the solution is heated for half an hour under the reflux. After cooling, the crystals are removed by filtration, recrystallized from glacial acetic acid, and 3,4-dihydro-2-methyl-3-oxo-4-(2-thiazolyl-carbamoyl)2H-thieno[ 2,3-e] 1,2-thiazine 1,1-dioxide, melting point 236° C. to 238° C. (decomposition), is obtained.

Workup

  1. temperatureAfter cooling
  2. customthe crystals are removed by filtration
  3. customrecrystallized from glacial acetic acid, and 3,4-dihydro-2-methyl-3-oxo-4-(2-thiazolyl-carbamoyl)2H-thieno[ 2,3-e] 1,2-thiazine 1,1-dioxide, melting point 236° C. to 238° C. (decomposition)
  4. customis obtained

Sources & evidence

ORD record
ord-a2132c149ac74cbf8bed3dce2c9cb808
Source dataset
uspto-grants-1978_05
Patent number
US04090020

Reaction notes

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