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

HRID 224598Notes

Reaction equation

HRID 224598 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[S:20][C:21]([CH3:24])=[CH:22][N:23]=1>>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:12])(=[O:13])[NH:4][C:3]=1[C:14]([NH:18][C:19]1[S:20][C:21]([CH3:24])=[CH:22][N:23]=1)=[O:16]

Participants

3

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 54676531methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 546906574-Hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 31%

Procedure

Prepared from methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 2-amino-5-methyl-thiazole analogous to Example 1. The crude product (65% of theory) was purified by column chromatography (Merck-silica gel 60, particle size: 0.2-0.5 mm), using chloroform/ethanol (97:3) as eluant. 4-Hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide was obtained with a yield of 31% of theory.

Workup

  1. customThe crude product (65% of theory) was purified by column chromatography (Merck-silica gel 60, particle size: 0.2-0.5 mm)

Sources & evidence

ORD record
ord-99877623d8de48228eaf3f08218ef728
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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