Water → Bis[4-(dimethylamino)phenyl](phenyl)acetonitrile

HRID 552053

Reaction equation

HRID 552053 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:11]2[CH:19]=[CH:18][C:14](=[N+:15]([CH3:17])[CH3:16])[CH:13]=[CH:12]2)=[CH:6][CH:5]=1)[CH3:3].[Cl-].[C-:27]#[N:28].[Na+].O.C(OCC)C>C(OCC)(=O)C>[CH3:1][N:2]([CH3:3])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:11]2[CH:12]=[CH:13][C:14]([N:15]([CH3:17])[CH3:16])=[CH:18][CH:19]=2)[C:27]#[N:28])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 11294Malachite Green

Product 1

HCID 220592Bis[4-(dimethylamino)phenyl](phenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Commercially obtained Malachite Green, oxalate salt (4.644 g) and sodium cyanide (2.456 g) were combined, followed by addition of water (150 mL) and diethyl ether (150 mL). The mixture was rapidly stirred for three hours, at which point the green color had faded, and the mixture was a muddy brown. The mixture was transferred to a separatory funnel with the aid of ethyl acetate, partitioned, and the aqueous phase extracted with three portions of ethyl acetate (100 mL each). The combined organics were washed once with brine (50 mL), dried over sodium sulfate, filtered and concentrated by rotary evaporation to provide crude nitrile 3A contaminated by some of the triarylcarbinol.

Workup

  1. custompartitioned
  2. extractionthe aqueous phase extracted with three portions of ethyl acetate (100 mL each)
  3. washThe combined organics were washed once with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6ecb6c9e28ab4782b49b55b5e39969ee
Source dataset
uspto-grants-2011_05
Patent number
US07951607B2

Linked notes

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