Suprofen → HCID 21391741, compound

HRID 258916Notes

Reaction equation

HRID 258916 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.[H-].[Na+].[Cl:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]>CN(C)P(N(C)C)(N(C)C)=O>[ClH:21].[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([O:15][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5359SuprofenHCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydride

Product 1

HCID 21391741HCID 21391741, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 10.4 parts of p-(2-thenoyl)hydratropic acid in 75 parts of hexamethylphosphoramide is heated to 50° C and there are added 1.3 parts of sodium hydride dispersion 78.3%. When the reaction is ceased, there are added 10 parts of N-(2-chloroethyl)-N,N-diethylamine and the whole is stirred overnight at 50° C. The reaction mixture is cooled and extracted with 240 parts of benzene and 100 parts of water. The organic layer is washed with diluted sodium hydroxide solution and with water, dried and evaporated. The oily residue is converted into the hydrochloride salt in 2-propanol. After cooling to -20° C, the precipitated salt is filtered off and dried, yielding 2-(diethylamino)ethyl p-(2-thenoyl)hydratropate hydrochloride; mp. 126.4° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with 240 parts of benzene and 100 parts of water
  3. washThe organic layer is washed with diluted sodium hydroxide solution and with water
  4. customdried
  5. customevaporated
  6. temperatureAfter cooling to -20° C
  7. filtrationthe precipitated salt is filtered off
  8. customdried

Sources & evidence

ORD record
ord-c0a6f7cbfca54c349be5f7629cda4434
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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