1-[4-(4-Hydroxyphenyl)butyl]imidazole → 2-(5-Bromo-4-methyl-2-thienyl)-4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazole

HRID 322421Notes

Reaction equation

HRID 322421 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[Br:17][C:18]1[S:22][C:21]([C:23]2[O:24][CH:25]=[C:26]([CH2:28]Cl)[N:27]=2)=[CH:20][C:19]=1[CH3:30]>>[Br:17][C:18]1[S:22][C:21]([C:23]2[O:24][CH:25]=[C:26]([CH2:28][O:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]4[CH:16]=[CH:15][N:14]=[CH:13]4)=[CH:4][CH:3]=3)[N:27]=2)=[CH:20][C:19]=1[CH3:30]

Participants

3

Reactant 2

HCID 220096641-[4-(4-Hydroxyphenyl)butyl]imidazoleHCID 220097082-(5-Bromo-4-methyl-2-thienyl)-4-chloromethyloxazole

Product 1

HCID 220096732-(5-Bromo-4-methyl-2-thienyl)-4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazoleYield 93%

Procedure

In substantially the same manner as in Working Example 72, 1-[4-(4-hydroxyphenyl)butyl]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-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazole. The yield was 93%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 85-86° C.

Sources & evidence

ORD record
ord-76f27ee4d07343f491fa5c7a573e9adc
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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