Water → HCID 68669331, compound

HRID 2184363Notes

Reaction equation

HRID 2184363 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.O>CC(CC)=O>[CH3:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:29][CH:28]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 544005703-(4-Hydroxyphenyl)-N-methylprop-2-enamide

Product 1

HCID 68669331HCID 68669331, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

195 mg (1.1 mmol) 3-(4-hydroxy-phenyl)-N-methyl-acrylamide is dissolved in 25 ml ethyl methyl ketone and 304 mg (2.2 mmol) potassium carbonate is added, followed by 289 mg (1.2 mmol) of 4-(trifluoromethyl)benzyl bromide. The reaction mixture is stirred overnight at RT, heated to 50° C. for 3 hours, treated with water and extracted 3 times with dichloromethane. The extract is dried over magnesium sulfate, concentrated and treated with ether to yield 260 mg (70%) of a colorless solid. MS: m/e=336.1 (M++H).

Workup

  1. temperatureheated to 50° C. for 3 hours
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated
  5. additiontreated with ether

Sources & evidence

ORD record
ord-e996b2e172934bdcb7d095a644c19511
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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