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

HRID 2184350노트

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HRID 2184350 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6e24374e65344b4b8ecacfa75efd3abc
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900354B2

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