5-Chloromethyl-2-(2-thienyl)benzoxazole → 5-[3-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)benzoxazole

HRID 322410Notes

Reaction equation

HRID 322410 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[O:25][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[N:23][C:22]=2[CH:31]=1>>[N:11]1([CH2:10][CH2:9][CH2:8][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[O:1][CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[O:25][C:24]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[N:23][C:22]=3[CH:31]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 220097205-Chloromethyl-2-(2-thienyl)benzoxazoleHCID 220098091-[3-(3-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220097855-[3-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)benzoxazoleYield 76%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(3-hydroxyphenyl)propyl]imidazole was allowed to react with 5-chloromethyl-2-(2-thienyl)benzoxazole to give 5-[3-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)benzoxazole. The yield was 76%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 86-87° C.

Sources & evidence

ORD record
ord-d55b1559c280404c9b9c9906b6d90cfb
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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