Water → 175225-48-6

HRID 660888Notes

Reaction equation

HRID 660888 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.I[CH3:15].[NH2-].[Na+].O>C1(C)C=CC=CC=1.ClCCl>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]([CH3:15])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24533Sodium amideHCID 75360m-Trifluoromethylphenylacetonitrile

Product 1

HCID 10845676175225-48-6

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g (5.4 mmol) of 3-(trifluoromethyl)phenylacetonitrile and 767 mg of iodomethane (5.4 mmol) are placed in 5 ml toluene at 80° C. and slowly treated with a 50% suspension of sodamide in toluene. Next the mixture is stirred 1 hr more at 80° C., then cooled to RT and treated with water, then dichloromethane. The organic phase is separated, washed with water, dried over magnesium sulphate and freed of solvent on the rotary evaporator. The residue (1.7 g, 84% of theory) contains the title compound with a purity of ca. 53% by GC/MS and is used without purification for the next reaction.

Workup

  1. temperaturecooled to RT
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customfreed of solvent on the rotary evaporator
  6. customis used without purification for the next reaction

Sources & evidence

ORD record
ord-77848d7e3975464fbb13ec4b9bd6c386
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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