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

HRID 362822ノート

反応式

HRID 362822 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b89f4fbba1b14f119cc7dfb0714fa327
出典データセット
uspto-grants-1999_02
特許番号
US05872118

反応ノート

読み込み中…