2-Amino-5-methylthiazole → 2,6-Dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

HRID 224599Notes

Reaction equation

HRID 224599 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=2[S:5](=[O:14])(=[O:13])[N:4]([CH3:15])[C:3]=1[C:16]([O:18]C)=O.[NH2:20][C:21]1[S:22][C:23]([CH3:26])=[CH:24][N:25]=1>C1(C)C(C)=CC=CC=1>[CH3:15][N:4]1[C:3]([C:16]([NH:20][C:21]2[S:22][C:23]([CH3:26])=[CH:24][N:25]=2)=[O:18])=[C:2]([OH:1])[C:7]2[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=2[S:5]1(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 54696079methyl 4-hydroxy-2,6-dimethyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide

Product 1

HCID 546942212,6-Dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.0 gm (14 millimols) of methyl 4-hydroxy-2,6-dimethyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 2.0 gm (17 millimols) of 2-amino-5-methyl-thiazole were refluxed in 200 ml of anhydrous xylene for 24 hours. After cooling, the crystals which had separated out were filtered off. After recrystallization from ethylene chloride 3.6 gm (70% of theory) of 2,6-dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3carboxamide-1,1-dioxide were obtained.

Workup

  1. temperatureAfter cooling
  2. customthe crystals which had separated out
  3. filtrationwere filtered off
  4. customAfter recrystallization from ethylene chloride 3.6 gm (70% of theory) of 2,6-dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3carboxamide-1,1-dioxide
  5. customwere obtained

Sources & evidence

ORD record
ord-193861cfc36a487aa1ee9cd683e467d0
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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