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

HRID 2184360Notes

Reaction equation

HRID 2184360 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15](Cl)=[O:16])=[CH:9][CH:8]=1.[CH3:21][NH2:22]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([NH:22][CH3:21])=[O:16])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 713776793-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-enoyl chloride

Product 1

HCID 686684993-{4-[(3-Fluorophenyl)methoxy]phenyl}-N-methylprop-2-enamideYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

500 mg (1.72 mmol) of the crude 3-[4-(3-fluoro-benzyloxy)-phenyl]-acryloyl chloride is dissolved in 2 ml dichloromethane and 0.4 ml of a 41% solution of methylamine in water is added. The reaction mixture is heated under reflux for about 3 hours, cooled, filtered and washed with cold dichloromethane to yield 149 mg (30%) of a colorless solid. MS: m/e=286.2 (M+).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for about 3 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed with cold dichloromethane

Sources & evidence

ORD record
ord-1f439d76a4bb4fbb8bfe9418063e8ebc
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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