Dicyclohexylcarbodiimide → HCID 21844481, compound

HRID 361933Notes

Reaction equation

HRID 361933 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[CH:8][C:7]=2[CH:22]=1)#[N:2].O[N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[N:25]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N:24]1([O:18][C:17]([C:16]2[CH:20]=[CH:21][C:13]([CH2:12][CH2:11][C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][C:7]=4[CH:8]=3)=[CH:14][CH:15]=2)=[O:19])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[N:25]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 218442934-[2-(5-Cyano-2-benzofuranyl)ethyl]benzoic acid

Product 1

HCID 21844481HCID 21844481, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1 g of 4-[2-(5-cyano-2-benzofuranyl)ethyl]benzoic acid and 578 mg of 1-hydroxybenzotriazole were dissolved in 100 ml of dichloromethane, followed by the addition of 780 mg of 1,3-dicyclohexylcarbodiimide and by subsequent stirring at the same temperature for 3 hours. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a chloroform/ethanol mixture as an elution solvent, and the thus purified product was crystallized from a benzene/n-hexane mixture. In this way, 1.1 g of 2-[2-[4-[[(1-benzotriazolyl)oxy]-carbonyl]phenyl]ethyl]-5-benzofurancarbonitrile was obtained in a powdery form.

Workup

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue was purified
  3. customthe thus purified product was crystallized from a benzene/n-hexane mixture

Sources & evidence

ORD record
ord-2b3a40c2d52b418db3794ef5b77f16c9
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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