4-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazole → 4-[2-Chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole

HRID 322464Notes

Reaction equation

HRID 322464 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[CH2:18][C:19]1[N:20]=[C:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[O:22][CH:23]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:18][C:19]1[N:20]=[C:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[O:22][CH:23]=1

Participants

3

Reactant 2

HCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleHCID 220098751-[3-(3-Chloro-4-hydroxyphenyl)propyl]imidazole

Product 1

HCID 220096434-[2-Chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazoleYield 77%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(3-chloro-4-hydroxyphenyl)propyl]imidazole was reacted with 4-chloromethyl-2-(2-thienyl)oxazole to obtain 4-[2-chloro-4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole. The yield was 77%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 93-94° C.

Sources & evidence

ORD record
ord-221b0a892f9847e5a2fd8012911e071c
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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