4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole → 2-(4-Chlorophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

HRID 322379Notes

Reaction equation

HRID 322379 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH:3]=1.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[O:21][CH:22]=1>>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[O:21][CH:22]=[C:18]([CH2:17][O:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]4[CH:15]=[CH:14][N:13]=[CH:12]4)=[CH:4][CH:3]=3)[N:19]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220096932-(4-Chlorophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazoleYield 76%

Procedure

In substantially the same manner as in Working Example 48, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 4-chloromethyl-2-(4-chlorophenyl) oxazole to give 2-(4-chlorophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole. The yield was 76%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 116-117° C.

Sources & evidence

ORD record
ord-3b4ed062b41343f0bee35c0e40e06a62
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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