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

HRID 2184350Notes

Reaction equation

HRID 2184350 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6e24374e65344b4b8ecacfa75efd3abc
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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