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

HRID 1448582Notes

Reaction equation

HRID 1448582 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][S: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]=[CH:9][S:10][C:6]=2[S:5](=[O:11])(=[O:12])[N:4]([CH3:13])[C:3]=1[C:14](=[O:16])[NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 546766134-hydroxy-2-methyl-3-methoxycarbonyl-2H-thieno[3,2-e]1,2-thiazine-1,1-dioxide

Product 1

HCID 547171094-hydroxy-2-methyl-3-(2-thiazolylcarbamoyl)-2H-thieno[3,2-e]1,2-thiazine-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.25 g. of 4-hydroxy-2-methyl-3-methoxycarbonyl-2H-thieno[3,2-e]1,2-thiazine-1,1-dioxide is heated under reflux for 17 hours with 0.14 g. of 2-aminothiazole in 28 ml. of absolute xylene, while passing a stream of nitrogen through the said mixture. The mixture is cooled to room temperature and crystallization of the product is initiated by scratching. The product is kept overnight in the cold. The precipitate crystals are removed by filtration under suction and recrystallized from ethanol, whereby 4-hydroxy-2-methyl-3-(2-thiazolylcarbamoyl)-2H-thieno[3,2-e]1,2-thiazine-1,1-dioxide having a melting point of 226°-227° (with decomposition) is obtained.

Workup

  1. temperatureunder reflux for 17 hours with 0.14 g
  2. customcrystallization of the product
  3. customThe precipitate crystals are removed by filtration under suction
  4. customrecrystallized from ethanol, whereby 4-hydroxy-2-methyl-3-(2-thiazolylcarbamoyl)-2H-thieno[3,2-e]1,2-thiazine-1,1-dioxide having a melting point of 226°-227° (with decomposition)
  5. customis obtained

Sources & evidence

ORD record
ord-a094e3b2ed8f4870bbfe44f55fb4443b
Source dataset
uspto-grants-1979_12
Patent number
US04180662

Reaction notes

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