Dimethyl Sulfate → Piroxicam

HRID 2291646Notes

Reaction equation

HRID 2291646 reaction equation
[Na].[S:2]1([C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[NH:5]1)(=[O:4])=[O:3].Cl[CH2:15][C:16](OC(C)C)=[O:17].[Na].S(OC)(O[CH3:27])(=O)=O.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>CN(C)C=O.C(O)(C)C.C1(C)C(C)=CC=CC=1>[OH:7][C:6]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[S:2](=[O:4])(=[O:3])[N:5]([CH3:27])[C:15]=1[C:16]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)=[O:17]

Participants

9

Reactant 5

HCID 6497Dimethyl SulfateHCID 7759Isopropyl chloroacetateHCID 104392-AminopyridineHCID 5360545SodiumHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 54676228Piroxicam

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Procedure

By reacting saccharin sodium with isopropyl chloroacetate in dimethylformamide, isopropyl 3-oxo-1,2-bensoisothiazoline-2-acetate 1,1-dioxide is obtained which, by reaction with sodium isopropylate in isopropanol at temperatures between 60° C. and the boiling point of the solvent, for a time between 15 minutes and 3 hours, leads to a compound which, when methylated in an aqueous-alcoholic basic medium with dimethyl sulfate, gives an intermediate compound which, when condensed with 2-aminopyridine in xylene, yields 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide which may be used as a non-steroidal analgesic and anti-inflammatory drug.

Workup

  1. customis obtained which
  2. customfor a time between 15 minutes and 3 hours
  3. customgives

Sources & evidence

ORD record
ord-b83aa681c18348a086bdc56a36d55348
Source dataset
uspto-grants-1989_01
Patent number
US04797483

Reaction notes

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