Hydrochloric Acid → Suprofen

HRID 258904

Reaction equation

HRID 258904 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 part of (+)-p-(2-thenoyl)hydratropic acid α-methylbenzylamine is suspended in water and acidified with hydrochloric acid. The product is extracted with ether. The organic layer is washed with water, dried, filtered and evaporated in vacuo. The oily residue solidifies on triturating in petroleumether. The solidified product is filtered off and dried in vacuo at 50° C, yielding (-)-p-(2-thenoyl)hydratropic acid; [α] (1% MeOH) =MeOH)= -45.6°.

Workup

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

Sources & evidence

ORD record
ord-2c53f8e24b814c87a7c9ecb3767b3d63
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Linked notes

Loading…