1-[3-(3-Chloro-4-hydroxyphenyl)propyl]imidazole → 4-[2-Chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole

HRID 322465Notes

Reaction equation

HRID 322465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[CH2:18][C:19]1[N:20]=[C:21]([C:24]2[S:25][C:26]([CH3:29])=[CH:27][CH:28]=2)[O:22][CH:23]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:18][C:19]1[N:20]=[C:21]([C:24]2[S:25][C:26]([CH3:29])=[CH:27][CH:28]=2)[O:22][CH:23]=1

Participants

3

Reactant 2

HCID 220098751-[3-(3-Chloro-4-hydroxyphenyl)propyl]imidazoleHCID 222414544-Chloromethyl-2-(5-methyl-2-thienyl)oxazole

Product 1

HCID 220095934-[2-Chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazoleYield 83%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(3-chloro-4-hydroxyphenyl)propyl]imidazole was reacted with 4-chloromethyl-2-(5-methyl-2-thienyl)oxazole to obtain 4-[2-chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole. The yield was 83%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 95-96° C.

Sources & evidence

ORD record
ord-a850f78fa90541bba3f9d61cf783c027
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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