Water → HCID 13236172, compound

HRID 648127Notes

Reaction equation

HRID 648127 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20]Cl)=[CH:9][CH:8]=1)[CH3:6].O.[CH3:23][N:24](C)C=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][C:23]#[N:24])=[CH:9][CH:8]=1)[CH3:6])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 8929Sodium CyanideHCID 13236171HCID 13236171, compound

Product 1

HCID 13236172HCID 13236172, compound

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Sodium cyanide (2.4 g) and 0.8 g of benzyl triethyl ammonium chloride were added to 30 ml of dimethyl formamide, and with stirring, a solution of 5.6 g of (1-chloroethyl)-4-(2-chloromethylbenzyl)benzene in 10 ml of dimethyl formamide was added. The mixture was stirred at 40° C. for 1 hour and then at 70° C. for 20 hours. After the reaction, the reaction mixture was cooled, and 70 ml of water was added. The mixture was extracted with ether. The ethereal layer was washed with water, dried over anhydrous magnesium sulfate and distilled off to remove the ether. The resulting pale yellow oily substance was chromatographed on a silica gel column using benzene as an eluent. From the eluate, 3.4 g of (1-cyanoethyl)-4-(2-cyanomethylbenzyl)benzene was obtained as a colorless liquid. This compound crystallized by stimulating the reactor wall through addition of n-hexane. Recrystallization from a mixture of ether and n-hexane afforded colorless needle-like crystals having a melting point of 61° to 64° C.

Workup

  1. stirringThe mixture was stirred at 40° C. for 1 hour
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled
  4. extractionThe mixture was extracted with ether
  5. washThe ethereal layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled off
  8. customto remove the ether
  9. customThe resulting pale yellow oily substance was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-79aed0a2f6c44987af11944242e04c08
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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