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

HRID 484684Notes

Reaction equation

HRID 484684 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]([O:17]C)=O.[NH2:19][C:20]1[CH:25]=[N:24][CH:23]=[C:22]([Cl:26])[N:21]=1.C1(C)C(C)=CC=CC=1>CO>[Cl:26][C:22]1[N:21]=[C:20]([NH:19][C:15]([C:3]2[N:4]([CH3:14])[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:17])[CH:25]=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 1184582-Amino-6-ChloropyrazineHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 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 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.0 g (33 mmols) of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide, 4.36 g (33 mmols) of 2-amino-6-chloro-pyrazine and 1200 ml of xylene was refluxed for 24 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 and standing overnight, the crystals were filtered off and recrystallized from dioxane. 7.91 g (64% of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained.

Workup

  1. temperaturewas refluxed for 24 hours in a nitrogen atmosphere
  2. customwas removed with the aid of a 4 Å molecular sieve
  3. temperatureAfter cooling
  4. filtrationthe crystals were filtered off
  5. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-a74c2565ecc84019b608b860d010d7e7
Source dataset
uspto-grants-1985_08
Patent number
US04533664

Reaction notes

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