Water → HCID 70544649, 화합물

HRID 1759249노트

반응식

HRID 1759249 반응식
[H-].[Na+].[OH:3][C:4]1[C:5]([CH2:10][C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.O>CN(C)C=O.C(OCC)C>[CH2:25]([O:24][C:22]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:3][C:4]2[C:5]([CH2:10][C:11]3[NH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:28][CH:27]=1)=[O:23])[CH3:26]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 70545010HCID 70545010, 화합물

생성물 1

HCID 70544649HCID 70544649, 화합물수율 42%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (1.81 g of 50% dispersion in mineral oil) was added in portions to a stirred solution of 3-hydroxy-2-(1-imidazolylmethyl)pyridine (6.00 g) in dry N,N-dimethylformamide (100 ml) at 0° C. The mixture was stirred for 15 minutes and a solution of ethyl 4-bromomethyl-benzoate (8.34 g) in dry N,N-dimethylformamide (20 ml) was then added over a period of 10 minutes. The mixture was allowed to warm to room temperature, stirred for 4 hours and water (5 ml) was then added. The solution was evaporated and the residue chromatographed on silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated to give an oil which solidified on trituration with diethyl ether. Recrystallization from diethyl ether gave 3-(4-ethoxycarbonylbenzyloxy)-2-(1-imidazolylmethyl)pyridine (4.85 g), m.p. 100°-101° C.

후처리

  1. stirringstirred for 4 hours
  2. customThe solution was evaporated
  3. customthe residue chromatographed on silica gel
  4. washeluting with chloroform
  5. customevaporated
  6. customto give an oil which
  7. customRecrystallization from diethyl ether

출처 및 근거

ORD 기록
ord-a41b42966c4f422b88544b910eb4db3b
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04339583

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