Dimethylamine → 2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile

HRID 968078

Reaction equation

HRID 968078 reaction equation
[CH3:1][NH:2][CH3:3].S(=O)(=O)(O)O.[C-:9]#[N:10].[Na+].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1>O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]([N:2]([CH3:3])[CH3:1])[C:9]#[N:10])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 113098562-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrileYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 l four-necked flask equipped with a thermometer, a stirrer and a dropping funnel, 144.5 g (1.6 mol) of a 50.7% dimethylamine aqueous solution and 118.5 g of water were charged, and 159.4 g (0.38 mol) of a 25% of sulfuric acid aqueous solution was dropwise added over a period of 15 minutes at a temperature of not higher than 20° C. with stirring. Then, 67.4 g (1.38 mol) of sodium cyanide was introduced. Then, 155.1 g (1.25 mol) of 4-fluorobenzaldehyde was dropwise added over a period of 20 minutes at from 20 to 30° C. Thereafter, the reaction was carried out at 50° C. for 4 hours. After completion of the reaction, the reaction mixture was subjected to liquid separation. The organic layer was separated and washed with 500 ml of water of 50° C. to obtain 222.8 g (yield: 98.4%) of the desired compound having a purity of 98.4% (by GC analysis).

Workup

  1. additionwere charged
  2. customAfter completion of the reaction
  3. customthe reaction mixture was subjected to liquid separation
  4. customThe organic layer was separated
  5. washwashed with 500 ml of water of 50° C.

Sources & evidence

ORD record
ord-812e62ea85a7484cbe5e45f6336653c1
Source dataset
uspto-grants-2005_10
Patent number
US06956132B2

Linked notes

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