Suprofen → HCID 3642305, compound

HRID 258931Notes

Reaction equation

HRID 258931 reaction equation
[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[Na].[CH3:20]N(C)P(N(C)C)(N(C)C)=O.CI>O>[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([O:15][CH3:20])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5359SuprofenHCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 5360545Sodium

Product 1

HCID 3642305HCID 3642305, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 28.2 parts of p-(2-thenoyl)hydratropic acid, sodium salt and 250 parts of hexamethylphosphoramide are added 56.8 parts of methyl iodide at room temperature (slightly exothermic reaction). The whole is stirred at room temperature for one hour. The reaction mixture is poured onto 1000 parts of water and the product is extracted three times with 140 parts of diisopropylether. The combined extracts are washed with 200 parts of water, dried, filtered and evaporated. The residue is crystallized from 35 parts of diisopropylether at 0° C, washed with cooled ether and dried, yielding methyl p-(2-thenoyl)hydratropate; mp. 62° C.

Workup

  1. customslightly exothermic reaction)
  2. extractionthe product is extracted three times with 140 parts of diisopropylether
  3. washThe combined extracts are washed with 200 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 35 parts of diisopropylether at 0° C
  8. washwashed with cooled ether
  9. customdried

Sources & evidence

ORD record
ord-7fca6e50c27540e883774cef0d926cdc
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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