2-(2-Benzo[b]thienyl)-4-chloromethyl-5-methyloxazole → 2-(2-Benzo[b]thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazole

HRID 322375Notes

Reaction equation

HRID 322375 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.[S:16]1[C:20]([C:21]2[O:22][C:23]([CH3:28])=[C:24]([CH2:26]Cl)[N:25]=2)=[CH:19][C:18]2[CH:29]=[CH:30][CH:31]=[CH:32][C:17]1=2>>[S:16]1[C:20]([C:21]2[O:22][C:23]([CH3:28])=[C:24]([CH2:26][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:25]=2)=[CH:19][C:18]2[CH:29]=[CH:30][CH:31]=[CH:32][C:17]1=2

Participants

3

Reactant 2

HCID 220096492-(2-Benzo[b]thienyl)-4-chloromethyl-5-methyloxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220097182-(2-Benzo[b]thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazoleYield 38%

Procedure

In substantially the same manner as in Working Example 37, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 2-(2-benzo[b]thienyl)-4-chloromethyl-5-methyloxazole to give 2-(2-benzo[b]thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazole. The yield was 38%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 142-143° C.

Sources & evidence

ORD record
ord-b767b9d5317c41f78241fc6935b21987
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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