Ammonium Hydroxide → HCID 23342972, compound

HRID 27448Notes

Reaction equation

HRID 27448 reaction equation
C([S:4][CH2:5][CH2:6][C:7]([N:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10]1)=[O:8])(=O)C.[OH-].[NH4+]>>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:10]1)=[O:8]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 23342963HCID 23342963, compound

Product 1

HCID 23342972HCID 23342972, compoundYield 69.1%

Procedure

DL-4,5-Dihydro-1-[3-(acetylthio)-1-oxopropyl]-3-phenyl-1H-pyrazole-5-carboxylic acid (6.0g) is treated in an argon atmosphere with 40ml of a cold solution of 6.5N ammonium hydroxide. After 30 minutes at room temperature, the solution is washed with ethyl acetate, treated with concentrated hydrochloric acid to pH 2.5 and extracted with ethyl acetate. The extract is dried over magnesium sulfate and concentrated in vacuo to an oil. Trituration of the oil with ether yields 3.6g of the title compound, melting point 118°-120° C.

Workup

  1. washthe solution is washed with ethyl acetate
  2. additiontreated with concentrated hydrochloric acid to pH 2.5
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-20b880f4e49545f3a7dd57e311f0990e
Source dataset
uspto-grants-1980_09
Patent number
US04221804

Reaction notes

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