Dicyclohexylcarbodiimide → HCID 18953956, compound

HRID 2255228Notes

Reaction equation

HRID 2255228 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[C:18]1([C:24](O)([CH3:26])[CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([O:17][C:24]([CH3:26])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:25])=[O:16])[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 120532-Phenyl-2-propanol2×HCID 18953969HCID 18953969, compound

Product 1

HCID 18953956HCID 18953956, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-2-oxazolepropionic acid (0.5 g) in acetonitrile (20 ml) were added 2-phenyl-2-propanol (0.325 g), dicyclohexylcarbodiimide (0.49 g) and 4-dimethylaminopyridine (0.025 g), followed by stirring for 65 hours at room temperature. 2-Phenyl-2-propanol (0.325 g), dicyclohexylcarbodiimide (0.49 g) and 4-dimethylaminopyridine (0.025 g) were further added to the reaction mixture, followed by stirring for 2 hours at 50° C. The reaction mixture was filtered to remove an insoluble substance, and the filtrate was then concentrated. The oily residue was subjected to a silica gel column chromatography. Crystals of 1-methyl-1-phenylethyl 4-(4-chlorophenyl)-2-oxazolepropionate (0.297 g, 38%) were obtained from the fraction eluted with ethyl acetate-hexane (1:4, V/V). Recrystallization from hexane gave colorless prism crystals of mp 94°-95° C.

Workup

  1. stirringby stirring for 2 hours at 50° C
  2. filtrationThe reaction mixture was filtered
  3. customto remove an insoluble substance
  4. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-1f306d98f4644037b6a5d7df6dc2fb14
Source dataset
uspto-grants-1993_08
Patent number
US05239080

Reaction notes

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