4-(Chloromethyl)-2-(thiophen-2-yl)-1,3-thiazole → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)thiazole

HRID 322415Notes

Reaction equation

HRID 322415 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[S:24][CH:25]=[CH:26][CH:27]=2)[S:21][CH:22]=1>>[N:11]1([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:17][C:18]3[N:19]=[C:20]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[S:21][CH:22]=3)=[CH:3][CH:4]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 7364964-(Chloromethyl)-2-(thiophen-2-yl)-1,3-thiazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220097624-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)thiazoleYield 79%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 4-chloromethyl-2-(2-thienyl)thiazole to give 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)thiazole. The yield was 79%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 76-77° C.

Sources & evidence

ORD record
ord-1c13d128ade74ddab040b0a2ffe193c8
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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