Water → N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

HRID 484690Notes

Reaction equation

HRID 484690 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[N:4]([CH3:14])[C:3]=1[C:15](Cl)=[O:16].[NH2:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=1.O>CN(C)C=O>[Cl:25][C:21]1[N:20]=[C:19]([NH:18][C:15]([C:3]2[N:4]([CH3:14])[S:5](=[O:13])(=[O:12])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:16])[CH:24]=[N:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1184582-Amino-6-ChloropyrazineHCID 886983124-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide

Product 1

HCID 54703135N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 24.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.23 g (4.5 mmols) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide were dissolved in 10 ml of dimethylformamide, and 1.3 g (10 mmols) of 2-amino-6-chloro-pyrazine were added in portions thereto. The reaction mixture was stirred for 24 hours at room temperature and was then mixed with 40 ml of water. The aqueous mixture was stirred for 20 minutes at room temperature, and then the precipitate which had formed was filtered off, washed and dried. Recrystallization from dioxane yielded 0.4 g (24% of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.

Workup

  1. stirringThe aqueous mixture was stirred for 20 minutes at room temperature
  2. customthe precipitate which had formed
  3. filtrationwas filtered off
  4. washwashed
  5. customdried
  6. customRecrystallization from dioxane

Sources & evidence

ORD record
ord-238201fd33364c6192a786d0f2b0c4ec
Source dataset
uspto-grants-1985_08
Patent number
US04533664

Reaction notes

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