Dicyclohexylcarbodiimide → HCID 18650846, compound

HRID 1589766Notes

Reaction equation

HRID 1589766 reaction equation
[Cl:1][C@@H:2]([CH3:20])[CH2:3][C@H:4]([CH3:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:21]([C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)#[N:22].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl>[Cl:1][C@@H:2]([CH3:20])[CH2:3][C@H:4]([CH3:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 120874-Cyanobenzoic acidHCID 755674-PyrrolidinopyridineHCID 18650843HCID 18650843, compound

Product 1

HCID 18650846HCID 18650846, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.30 g of (S,S)-4-[4-(3"-chloro-1"-methylbutoxy)-phenyl]phenol, 0.16 g of 4-cyanobenzoic acid, 0.22 g of dicyclohexylcarbodiimide, 0.04 g of 4-pyrrolidinopyridine and 6 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 n-hexane and ethyl acetate (7:3) as a developing solvent to thereby give 0.2 g of 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 n-hexane and ethyl acetate (7:3) as a developing solvent

Sources & evidence

ORD record
ord-44bddf85e63b4d838f66672368c3ff42
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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