2-(5-Bromo-4-methyl-2-thienyl)-4-chloromethyloxazole → 2-(5-Bromo-4-methyl-2-thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

HRID 322420

Reaction equation

HRID 322420 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.[Br:16][C:17]1[S:21][C:20]([C:22]2[O:23][CH:24]=[C:25]([CH2:27]Cl)[N:26]=2)=[CH:19][C:18]=1[CH3:29]>>[Br:16][C:17]1[S:21][C:20]([C:22]2[O:23][CH:24]=[C:25]([CH2:27][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:26]=2)=[CH:19][C:18]=1[CH3:29]

Participants

3

Reactant 2

HCID 220097082-(5-Bromo-4-methyl-2-thienyl)-4-chloromethyloxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220095972-(5-Bromo-4-methyl-2-thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazoleYield 77%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 2-(5-bromo-4-methyl-2-thienyl)-4-chloromethyloxazole to give 2-(5-bromo-4-methyl-2-thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole. The yield was 77%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 92-93° C.

Sources & evidence

ORD record
ord-f9c4970ae65b4b01a2e4dbac6d907b6e
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Linked notes

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