Hydrogen Bromide → Meloxicam

HRID 224609Notes

Reaction equation

HRID 224609 reaction equation
Br.C[O:3][C:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7](=[O:15])(=[O:14])[N:6]([CH3:16])[C:5]=1[C:17]([NH:19][C:20]1[S:21][C:22]([CH3:25])=[CH:23][N:24]=1)=[O:18]>C(O)(=O)C>[OH:3][C:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7](=[O:15])(=[O:14])[N:6]([CH3:16])[C:5]=1[C:17]([NH:19][C:20]1[S:21][C:22]([CH3:25])=[CH:23][N:24]=1)=[O:18]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 23331598O-Methyl Meloxicam

Product 1

HCID 54677470Meloxicam

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 ml of 48% hydrobromic acid and 1 ml of glacial acetic acid were added to 0.2 gm (0.55 millimols) of 4-methoxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-caboxamide-1,1-dioxide. After standing for 24 hours, the reaction mixture was heated for two hours on a water bath and was subsequently evaporated in vacuo to dryness. The residue was dissolved in methylene chloride, and the solution was washed with water. After drying and evaporating of the organic phase, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide was obtained with a yield of 0.1 gm (52% of theory).

Workup

  1. temperaturethe reaction mixture was heated for two hours on a water bath
  2. customwas subsequently evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe solution was washed with water
  5. customAfter drying
  6. customevaporating of the organic phase

Sources & evidence

ORD record
ord-d7329cedddb3408a8e1d2fb81ea7303b
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

Loading…