Fumaric Acid → HCID 19031552, compound

HRID 266877Notes

Reaction equation

HRID 266877 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2([C:21](=[O:30])[CH2:22][S:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH2:20][CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[Cl:16]>C(O)C.CCOCC>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2([C:21](=[O:30])[CH2:22][S:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH2:20][CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 9863685HCID 9863685, compound

Product 1

HCID 19031552HCID 19031552, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of fumaric acid (0.65 g) in hot ethanol (20 ml) was added to a solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino) propylthio]ethanone (2.1 g, prepared by basification of the hydrochloride salt obtained in a similar manner to that described in Example 7) in ether (10 ml) and the mixture was allowed to stand at 4° C. for 96 hours. No solid precipitated, so the solvents were removed in vacuo to leave a brown oil which was triturated with petroleum ether (b.p. 40°-60° C.). The resulting solid was collected by filtration, washed with ether, dried in vacuo at ambient temperature for 18 hours, and recrystallised from a 3:2 mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.). The resulting solid was collected by filtration, washed with petroleum ether (b.p. 60°-80° C.), and dried in vacuo at ambient temperature for 18 hours to give 1-[1-(3,4-dichloro-phenyl)cyclobutyl]-2-[3-(dimethylamino)propylthio]ethanone fumarate as a white solid (1.1 g), m.p. 100°-103° C.

Workup

  1. customobtained in a similar manner to that
  2. customNo solid precipitated, so the solvents
  3. customwere removed in vacuo
  4. customto leave a brown oil which
  5. customwas triturated with petroleum ether (b.p. 40°-60° C.)
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with ether
  8. customdried in vacuo at ambient temperature for 18 hours
  9. customrecrystallised from a 3:2 mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)
  10. filtrationThe resulting solid was collected by filtration
  11. washwashed with petroleum ether (b.p. 60°-80° C.)
  12. customdried in vacuo at ambient temperature for 18 hours

Sources & evidence

ORD record
ord-920995d102e84bcaaf9db55825efd39f
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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