Dicyclohexylcarbodiimide → HCID 17912566, compound

HRID 963550Notes

Reaction equation

HRID 963550 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]([F:25])=[CH:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O.[C:26]1([S:32][C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[C:26]1([S:32][C:33]2[CH:39]=[CH:38][C:36]([NH:37][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH:18]=[C:17]([F:16])[F:25])=[CH:35][CH:34]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 96081Aniline, p-(phenylthio)- (6CI,7CI,8CI)HCID 112980566,6-difluorohex-5-enoic Acid

Product 1

HCID 17912566HCID 17912566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At from 0° to 10°, 20.6 g of N,N'-dicyclohexylcarbodiimide are added, while stirring, in portions to 15 g of 6,6-difluorohex-5-enoic acid in 150 ml of dichloromethane. The mixture is stirred for a further 15 minutes under cooling and then 20.1 g of 4-phenylthioaniline are added in portions. The reaction mixture is stirred for 3 hours at room temperature and then filtered. The organic phase is washed with saturated sodium hydrogen carbonate solution and then dried over sodium sulfate. After concentration by evaporation, the residue is recrystallised from toluene/hexane, yielding the title compound having a melting point of from 80° to 81° (compound no. 2-1).

Workup

  1. temperatureunder cooling
  2. stirringThe reaction mixture is stirred for 3 hours at room temperature
  3. filtrationfiltered
  4. washThe organic phase is washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationAfter concentration
  7. customby evaporation
  8. customthe residue is recrystallised from toluene/hexane

Sources & evidence

ORD record
ord-f99dc6f0fe7b46c4a7ab630e86f43663
Source dataset
uspto-grants-1998_06
Patent number
US05763481

Reaction notes

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