Hydrochloric Acid → Piroxicam

HRID 1979980Notes

Reaction equation

HRID 1979980 reaction equation
[CH3:1][N:2]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:3]1(=[O:5])=[O:4].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:24])[CH2:22]Cl.[H-].[Na+].Cl>CN(C)C=O>[OH:13][C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:3](=[O:5])(=[O:4])[N:2]([CH3:1])[C:22]=1[C:21]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 272902-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 2894352-Chloro-N-pyridin-2-yl-acetamide

Product 1

HCID 54676228Piroxicam

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 590 mg. (3 mmole) of N-methylsaccharin and 1.02 g. (6 mmole) of N-(2-pyridyl)chloroacetamide in 3 ml. of dimethylformamide at 40° C. was added 250 mg. (10.3 mmole) of 99% sodium hydride portionwise over a period of one hour. The reaction mixture was allowed to stir at 40° C. for 2.5 hours and was then added to 100 ml. of 5% hydrochloric acid solution and 300 ml. of ice. The precipitate was filtered and dried to give 24 mg.

Workup

  1. additionwas then added to 100 ml
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customto give 24 mg

Sources & evidence

ORD record
ord-d1128dda8ca145a8b9be8bdefdaf23e6
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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