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

HRID 322394노트

반응식

HRID 322394 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aaa20e4594354ceca64fd08ab2acc231
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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