Water → Meloxicam

HRID 224606Notes

Reaction equation

HRID 224606 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[S:20][C:21]([CH3:24])=[CH:22][N:23]=1.O>CN(C)C=O>[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]([NH:18][C:19]1[S:20][C:21]([CH3:24])=[CH:22][N:23]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 3517702-Amino-5-methylthiazoleHCID 886983124-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide

Product 1

HCID 54677470Meloxicam

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.23 gm (4.5 millimols) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide were dissolved in 10 ml of dimethylformamide and 1.0 gm (9 millimols) of 2-amino-5-methyl-thiazole was added in portions. The reaction mixture was stirred at room temperature for 24 hours, and then 40 ml of water were added. The mixture was stirred at room temperature for 20 minutes, and the precipitate which had formed was filtered off, washed and dried. After recrystallization from ethylene chloride 0.4 gm (25% of theory) of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. customthe precipitate which had formed
  3. filtrationwas filtered off
  4. washwashed
  5. customdried
  6. customAfter recrystallization from ethylene chloride 0.4 gm (25% of theory) of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
  7. customwere obtained

Sources & evidence

ORD record
ord-94aacca60adb4215bd6a39f27983a0c0
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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