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

HRID 322462Notes

Reaction equation

HRID 322462 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][C:3]=1[O:16][CH3:17].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[O:23][CH:24]=1>>[N:11]1([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:19][C:20]3[N:21]=[C:22]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[O:23][CH:24]=3)=[C:3]([O:16][CH3:17])[CH:4]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleHCID 220095941-[3-(4-Hydroxy-3-methoxyphenyl)propyl]imidazole

Product 1

HCID 220097534-[4-[3-(1-Imidazolyl)propyl]-2-methoxyphenoxymethyl]-2-(2-thienyl)oxazoleYield 80%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(4-hydroxy-3-methoxyphenyl)propyl]imidazole was reacted with 4-chloromethyl-2-(2-thienyl)oxazole to obtain 4-[4-[3-(1-imidazolyl)propyl]-2-methoxyphenoxymethyl]-2-(2-thienyl)oxazole. The yield was 80%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 94-95° C.

Sources & evidence

ORD record
ord-05b10cec25384a0b8e5e2c737ca35ea7
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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