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

HRID 2184365Notes

Reaction equation

HRID 2184365 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15](O)=[O:16])=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[CH3:26][NH2:27]>ClCCl.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([NH:27][CH3:26])=[O:16])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 533963793-{4-[(3,4-Difluorophenyl)methoxy]phenyl}prop-2-enoic acid

Product 1

HCID 686690023-{4-[(3,4-Difluorophenyl)methoxy]phenyl}-N-methylprop-2-enamideYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

500 mg (1.72 mmol) 3-[4-(3,4-difluoro-benzyloxy)-phenyl]-acrylic acid is suspended in 5 ml dichloromethane. 0.62 ml (8.6 mmol) thionyl chloride is added and the reaction mixture heated overnight to 45° C. Concentration leaves a yellowish tar which is dissolved again in 10 ml dichloromethane and treated with 1.1 ml of a 33% solution of methylamine in ethanol. After heating at 45° C. for 3 hours, the reaction mixture is filtered and the filtrate concentrated. Chromatography (silica gel, dichloromethane/methanol) yields 136 mg (26%) of a colorless solid. MS: m/e=304.1 (M++H).

Workup

  1. temperaturethe reaction mixture heated overnight to 45° C
  2. concentrationConcentration
  3. customleaves a yellowish tar which
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-5d27f7a1983d4abe99dee252a3953b6d
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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