Hydrochloric Acid → Suprofen

HRID 461716Notes

Reaction equation

HRID 461716 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) = -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-dae41145302c49b9a7a5189caf9def06
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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