Potassium Hydroxide → Piroxicam potassium

HRID 37064Notes

Reaction equation

HRID 37064 reaction equation
[CH3:1][N:2]1[S:11](=[O:13])(=[O:12])[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]([OH:14])=[C:3]1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=1)=[O:16].[OH-].[K+:25]>CO>[CH3:1][N:2]1[S:11](=[O:13])(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O-:14])=[C:3]1[C:15]([NH:17][C:18]1[N:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].[K+:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54676228Piroxicam

Product 1

HCID 86278276Piroxicam potassiumYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

10 g of piroxicam was suspended in 83 g of methanol. To this suspension was added 1.95 g of 85% KOH at 15° to 20° C. The resulting solution was stirred for 30 minutes at the same temperature, filtered and evaporated to remove methanol. The residue was dissolved by adding 74.2 g of isopropyl alcohol and the resulting solution was stirred for one hour at 20° to 25° C. and then cooled to 0° C. to precipitate the solid product. The resulting solid was filtered, washed with 24.7 g of isopropyl alcohol and then dried in vacuum to obtain 9.4 g (Yield 84%) of piroxicam potassium.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customto remove methanol
  4. dissolutionThe residue was dissolved
  5. additionby adding 74.2 g of isopropyl alcohol
  6. stirringthe resulting solution was stirred for one hour at 20° to 25° C.
  7. customto precipitate the solid product
  8. filtrationThe resulting solid was filtered
  9. washwashed with 24.7 g of isopropyl alcohol
  10. customdried in vacuum

Sources & evidence

ORD record
ord-3ea0abcb70e04f30b066fe9ef4b33779
Source dataset
uspto-grants-1995_05
Patent number
US05420124

Reaction notes

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