Ammonia → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}-2-methylprop-2-enamide

HRID 2184350ノート

反応式

HRID 2184350 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]([CH3:18])[C:15](O)=[O:16])=[CH:9][CH:8]=1.C(Cl)(=O)C(Cl)=O.[NH3:28]>ClCCl.CN(C)C=O.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]([CH3:18])[C:15]([NH2:28])=[O:16])=[CH:9][CH:8]=1

参加物

7

反応物 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 692894943-{4-[(3-Fluorophenyl)methoxy]phenyl}-2-methylprop-2-enoic acid

生成物 1

HCID 692897013-{4-[(3-Fluorophenyl)methoxy]phenyl}-2-methylprop-2-enamide収率 65%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

305 mg (1.07 mmol) of 3-[4-(3-fluoro-benzyloxy)-phenyl]-2-methyl-acrylic acid is dissolved in 8 ml of dichloromethane and one drop of dimethylformamide is added. The solution is cooled to 0° C. and treated dropwise with 676 mg (5.33 mmol) oxalyl chloride. The resulting solution is stirred at 0° C. for additional 30 minutes, then 2 hours at RT. Evaporation of the solvent leaves the crude acid chloride which is dissolved in 5 ml THF. This solution is slowly added under stirring to 10 ml of concentrated ammonia. The precipitate is filtered off and recrystallised from methanol to yield 199 mg (65%) of a colorless solid. MS: m/e=286.2 (M++H).

後処理

  1. custom2 hours
  2. customat RT
  3. customEvaporation of the solvent
  4. customleaves the crude acid chloride which
  5. additionThis solution is slowly added
  6. filtrationThe precipitate is filtered off
  7. customrecrystallised from methanol

出典と根拠

ORDレコード
ord-6e24374e65344b4b8ecacfa75efd3abc
出典データセット
uspto-grants-2005_05
特許番号
US06900354B2

反応ノート

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