Dicyclohexylcarbodiimide → HCID 18993837, compound

HRID 375014Notes

Reaction equation

HRID 375014 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=1[F:25])#[N:17].[C:26]([O:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=1)(=[O:30])/[CH:27]=[CH:28]/[CH3:29]>CN(C)C1C=CN=CC=1.ClCCl>[C:26]([O:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([O:24][C:21]2[CH:22]=[CH:23][C:18]([C:16]#[N:17])=[C:19]([F:25])[CH:20]=2)=[O:37])=[CH:39][CH:40]=1)(=[O:30])/[CH:27]=[CH:28]/[CH3:29]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 18993862HCID 18993862, compound

Product 1

HCID 18993837HCID 18993837, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.6 g of N,N'-dicyclohexylcarbodiimide were added while stirring within 5 minutes to a solution of 1.2 g of 4-cyano-3-fluorophenol, 1.2 g of 4-[(E)-but-2-enoyloxy]benzoic acid and 0.1 g of 4-(dimethylamino)pyridine in 50 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered. The filtrate was washed with saturated sodium bicarbonate solution and with water and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) and two-fold recrystallization of the fractions which were pure according to thin-layer chromatography gave 2.0 g of 4-cyano-3-fluorophenyl 4-[(E)-but-2-enoyloxy]benzoate. M.p. (C-N) 125° C. and cl.p. (N-I) 195° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with saturated sodium bicarbonate solution and with water
  3. concentrationconcentrated
  4. customChromatographic purification of the residue on silica gel
  5. customwith hexane/ethyl acetate (vol. 9:1) and two-fold recrystallization of the fractions which

Sources & evidence

ORD record
ord-0d34acd053e949b08ada17bd72a9b484
Source dataset
uspto-grants-1996_01
Patent number
US05484551

Reaction notes

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