Hydrochloric Acid → Suprofen

HRID 258902

Reaction equation

HRID 258902 reaction equation
CC(N)C1C=CC=CC=1.[C:10]1([C:15]([C:17]2[CH:27]=[CH:26][C:20]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[O:16])[S:14][CH:13]=[CH:12][CH:11]=1.Cl>O>[C:10]1([C:15]([C:17]2[CH:27]=[CH:26][C:20]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[O:16])[S:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70638167(+)-p-(2-Thenoyl)hydratropic acid alpha-methylbenzylamine

Product 1

HCID 5359Suprofen

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 Parts of (-)-p-(2-thenoyl)hydratropic acid α-methyl-benzylamine are suspended in water and acidified with hydrochloric acid. The product is extracted with ether. The organic layer is washed with water, dried and evaporated. The oily residue solidifies on triturating in petroleumether. The solified product is filtered off and dried in vacuo at 50° C, yielding (+)-p-(2-thenoyl)hydratropic acid; [α] (1% in MeOH) = +44.5°.

Workup

  1. extractionThe product is extracted with ether
  2. washThe organic layer is washed with water
  3. customdried
  4. customevaporated
  5. customon triturating in petroleumether
  6. filtrationThe solified product is filtered off
  7. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-05456246330d4b0294a5e89fa2698254
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Linked notes

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