4-Chlorobenzyl cyanide → HCID 57202579, compound

HRID 1278058Notes

Reaction equation

HRID 1278058 reaction equation
[C:1]([N+:5]1[CH2:9][CH2:8][CH2:7][C:6]=1OC)([CH3:4])([CH3:3])[CH3:2].COS([O-])(=O)=O.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][C:24]#[N:25])=[CH:21][CH:20]=1.[Na]>C(O)C>[C:1]([N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[C:23]([C:24]#[N:25])[C:22]1[CH:26]=[CH:27][C:19]([Cl:18])=[CH:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2415824-Chlorobenzyl cyanideHCID 5360545SodiumHCID 85945955HCID 85945955, compound

Product 1

HCID 57202579HCID 57202579, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat 56.8 g of 1-tert.-butyl-2-methoxy-1-pyrrolinium-methylsulfate and 30.3 g of 4-chlorobenzylcyanide to 80°. Add thereto (dropwise, within 2 hours, with stirring) a solution of 8.1 g of sodium in 160 ml of ethanol. After completion of the addition, boil the prepared admixture for a further 2 hours. Concentrate the boiled admixture and distil off (at 10-3 mm of Hg) the excess 4-chlorobenzylcyanide. Recrystallize the resulting residue from 170 ml of ethanol to obtain 11 g of the title compound. Concentrate the mother liquor to obtain a further 2.5 g (24% of theory) of the title compound in the form of light-brown crystals of m.p. 150° to 153°.

Workup

  1. additionAdd
  2. additionAfter completion of the addition
  3. customfor a further 2 hours
  4. concentrationConcentrate the boiled admixture
  5. customdistil off (at 10-3 mm of Hg) the excess 4-chlorobenzylcyanide
  6. customRecrystallize the resulting residue from 170 ml of ethanol

Sources & evidence

ORD record
ord-4c9ace16bf9a49f490f51ae49c0cc8cb
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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