Water → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole

HRID 322394Notes

Reaction equation

HRID 322394 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1.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.O>CN(C)C=O>[N:13]1([CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][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)=[CH:5][CH:6]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 98639314-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazoleYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (90 mg) was added to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (405 mg) in N,N-dimethyl formamide at room temperature and stirred for 1.5 hours. 4-Chloromethyl-2-(2-thienyl)oxazole (480 mg) was added, and the resultant was stirred at 90° C. for further 2 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 chromatography. From the fraction eluted with ethyl acetate-methanol (50:1, v/v), 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole (650 mg, 89%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 84-85° C.

Workup

  1. stirringthe resultant was stirred at 90° C. for further 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-methanol (50:1

Sources & evidence

ORD record
ord-aaa20e4594354ceca64fd08ab2acc231
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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