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

HRID 2184361Notes

Reaction equation

HRID 2184361 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.[NH3:21]>ClCCl>[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]([NH2:21])=[O:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 713776793-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-enoyl chloride

Product 1

HCID 692892063-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-enamideYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.72 mmol) of the crude 3-[4-(3-fluoro-benzyloxy)-phenyl]-acryloyl chloride as prepared in Example 8c) is dissolved in 2 ml dichloromethane and 4 ml of concentrated ammonia is added. The mixture is hold at reflux temperature for about 4 hours, cooled and filtered. The solid is subjected to column chromatography (silica gel, dichloromethane/methanol/ammonia 140:10:1) to give 89 mg (19%) of a colorless solid. MS: m/e=272.2 (M++H).

Workup

  1. temperatureat reflux temperature for about 4 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-283575db844d4b90a441e9780c22f9e1
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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