Water → HCID 86697890, compound

HRID 1618977Notes

Reaction equation

HRID 1618977 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[CH2:12]([NH:15][CH2:16][CH:17]=[CH2:18])[CH:13]=[CH2:14].O>C(#N)C>[CH2:12]([N:15]([CH2:16][CH:17]=[CH2:18])[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 962WaterHCID 31279DiallylamineHCID 1202482-Chloro-4'-fluoroacetophenone

Product 1

HCID 86697890HCID 86697890, compoundYield 118.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-1-(4-fluorophenyl)ethanone (10 g, 57.4 mmol) is dissolved in acetonitrile (400 mL). The solution is cooled to 0° C. and diallylamine (15.6 mL, 126.2 mmol) is added. After 1 hour, the mixture is poured into water (500 mL) and extracted twice with ethyl acetate (400 mL). The organic extracts are combined, washed with brine (1×200 mL), dried over sodium sulfate, filtered, and concentrated to give the crude title compound (15.84 g, 118%). ES/MS (m/e): 234 (M+H).

Workup

  1. extractionextracted twice with ethyl acetate (400 mL)
  2. washwashed with brine (1×200 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72427e109bd44e13bb4a395639cbd71d
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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