O-Cresol → 4-(3,4-Dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-(2-methylphenoxy)propyl]oxazole

HRID 47941

Reaction equation

HRID 47941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[O:12][C:13]=2[CH2:14][CH2:15][CH2:16][OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[O:12][C:13]=2[CH2:14][CH2:15][CH2:16][O:17][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH3:24])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 335O-CresolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 234318024-(3,4-Dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol

Product 1

HCID 234318084-(3,4-Dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-(2-methylphenoxy)propyl]oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol (352 mg), 2-methylphenol (216 mg), tributylphosphine (405 mg) and tetrahydrofuran (10 mL) was added 1,1′-(azodicarbonyl)dipiperidine (450 mg) at room temperature, and the mixture was stirred for 1 h. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography. The title compound was obtained as crystals from an eluate from ethyl acetate-hexane (2:3, v/v). Recrystallization from acetone-isopropyl ether gave colorless prism crystals (271 mg, 61%). melting point: 116-117° C.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d399aad705d44d06903d68da31dc9da2
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

Loading…