Dicyclohexylcarbodiimide → HCID 18650834, compound

HRID 1589763Notes

Reaction equation

HRID 1589763 reaction equation
[Cl:1][CH:2]([CH3:16])[CH2:3][CH:4]([CH3:15])[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1.[C:17]([C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1)#[N:18].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:6]([O:5][C@@H:4]([CH3:15])[CH2:3][C@@H:2]([Cl:1])[CH3:16])=[CH:7][CH:8]=2)=[CH:21][CH:20]=1)#[N:18]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130194-CyanophenolHCID 20081233HCID 20081233, compound

Product 1

HCID 18650834HCID 18650834, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g of 4-(3'-chloro-1'-methylbutoxy)benzoic acid, 0.50 g of 4-cyanophenol, 0.93 g of dicyclohexylcarbodiimide, 0.10 g of 4-pyrrolydinopyridine and 10 ml of methylene chloride were stirred together at room temperature for five hours. The dicyclohexyl urea thus precipitated was filtered and the filtrate was desolvated. The crude product thus obtained was purified by silica gel column chromatography with the use of a mixture of ethyl acetate and n-hexane (1:4) as a developing solvent to thereby give the title compound.

Workup

  1. customThe dicyclohexyl urea thus precipitated
  2. filtrationwas filtered
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography with the use of a mixture of ethyl acetate and n-hexane (1:4) as a developing solvent

Sources & evidence

ORD record
ord-c83c95a9c90f4c63a6004064f883d90b
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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