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

HRID 484686Notes

Reaction equation

HRID 484686 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])[NH:4][C:3]=1[C:14]([O:16]C)=O.[NH2:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=1.C1(C)C(C)=CC=CC=1>CO>[Cl:25][C:21]1[N:20]=[C:19]([NH:18][C:14]([C:3]2[NH:4][S:5](=[O:12])(=[O:13])[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 7237O-XyleneHCID 1184582-Amino-6-ChloropyrazineHCID 54676531methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 135815570N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.1 g (20 mmols) of methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide, 3.0 g (23 mmols) of 2-amino-6-chloropyrazine and 400 ml of xylene was refluxed for 12 hours in a nitrogen atmosphere. The methanol formed by the reaction was removed with the aid of a 4 Å molecular sieve arranged in a Soxhlet attachment. After cooling, the reaction mixture was concentrated by evaporation, and the residue was purified by chromatography on a silicagel column, yielding 2.3 g (33% of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.

Workup

  1. temperaturewas refluxed for 12 hours in a nitrogen atmosphere
  2. customwas removed with the aid of a 4 Å molecular sieve
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated by evaporation
  5. customthe residue was purified by chromatography on a silicagel column

Sources & evidence

ORD record
ord-bcb10df01c7549939b1e99adc42db38e
Source dataset
uspto-grants-1985_08
Patent number
US04533664

Reaction notes

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