Dimethylformamide → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole

HRID 322429Notes

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.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[S:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[O:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:11]1([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:17][C:18]3[N:19]=[C:20]([C:23]4[S:24][C:25]([CH3:28])=[CH:26][CH:27]=4)[O:21][CH:22]=3)=[CH:3][CH:4]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[3-(4-hydroxyphenyl)propyl]imidazole (465 mg), 4-chloromethyl-2-(5-methyl-2-thienyl)oxazole (600 mg), potassium carbonate (315 mg) and N,N-dimethylformamide (15 ml) was stirred at 80° C. for 14 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (20:1, v/v), crystals of 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole (490 mg, 56%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 83-84° C.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
washFrom the fraction eluted with ethyl acetate-methanol (20:1

Sources & evidence

ORD record: ord-7aa90d127b0b4b6c8101ea8e0b63384e
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211215B1

Reaction notes

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