Ammonium Hydroxide → 2-(4,6-Difluoroindan-1-ylidene)-acetamide, (E)-

HRID 362822노트

반응식

HRID 362822 반응식
[OH-].[NH4+:2].[F:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7]/[C:8]/2=[CH:14]\[C:15](Cl)=[O:16]>ClCCl>[F:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7]/[C:8]/2=[CH:14]\[C:15]([NH2:2])=[O:16]

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 10977254(E)-2-(4,6-difluoro-1-indanylidene)acetyl Chloride

생성물 1

HCID 101766722-(4,6-Difluoroindan-1-ylidene)-acetamide, (E)-수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A 30% aqueous ammonium hydroxide solution (1.7 mL, 0.026 mol) was added dropwise to a stirred, chilled (ice bath) solution of (E)-2-(4,6-difluoro-1-indanylidene)acetyl chloride (2.97 g, 0.013 mol) in dichloromethane (50 mL). After 4.5 h the mixture was concentrated in vacuo and the residue was partitioned between 5% aqueous sodium bicarbonate solution and ethyl acetate. The ethyl acetate solution was washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo Chromatography on silica gel with ethyl acetate: hexanes (7:3)as eluent and trituration of the resulting solid with pentane gave 1.63 g (60%) of (E)-2-(4,6difluoro-1-indanylidene)acetamide as a white solid: mp 178°-180° C.; NMR (DMSO-d6): d 6.94-7.45 (m, 4H), 6.46 (s, 1H), 2.94-3.00, 3.21-3.27 (2 m's, 4H); steady-state nOe: irradiation at 6.46 d, observed 19% nOe at 7.26 d.

후처리

  1. concentrationAfter 4.5 h the mixture was concentrated in vacuo
  2. customthe residue was partitioned between 5% aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe ethyl acetate solution was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo Chromatography on silica gel with ethyl acetate

출처 및 근거

ORD 기록
ord-b89f4fbba1b14f119cc7dfb0714fa327
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872118

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