Cyanogen Chloride → HCID 54093259, compound

HRID 2163305Notes

Reaction equation

HRID 2163305 reaction equation
[CH2:1]([N:3]([CH2:11]C)[C:4](=[O:10])[CH2:5][C:6]([CH2:8][Cl:9])=[O:7])C.Cl[C:14]#[N:15]>O.C1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][N:3]([CH3:11])[C:4](=[O:10])[CH:5]([C:14]#[N:15])[C:6]([CH2:8][Cl:9])=[O:7]

Participants

6

Reactant 2

HCID 10477Cyanogen ChlorideHCID 21116160HCID 21116160, compound

Product 1

HCID 54093259HCID 54093259, compoundYield 75.3%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 241BenzeneSolvent3×HCID 962WaterSolvent

Procedure

10.0 gm. (0.05 mole) of copper acetate was dissolved hot in 150 ml of H2O and added to a solution of 19.1 gm. (0.1 mole) of γ-chloroacetoacetic acid diethyl amide in 150 ml of benzene. After brief stirring the green benzene solution was separated and dried over MgSO4. Then 6.2 gm. (0.1 mole) of ClCN were introduced into the benzene solution -- the temperature was kept at 20° to 30° C. The precipitated CuCl2 was filtered off and the benzene solution was precipitated. 14.2 gm of α-cyano-γ-chloroacetoacetic acid dimethylamide was obtained, which corresponds to 65.6 percent of theoretical.

Workup

  1. additionadded to a solution of 19.1 gm
  2. customwas separated
  3. dry with materialdried over MgSO4
  4. customwas kept at 20° to 30° C
  5. filtrationThe precipitated CuCl2 was filtered off
  6. customthe benzene solution was precipitated

Sources & evidence

ORD record
ord-48330b59d1704a0184a1ea4ac12f2b2c
Source dataset
uspto-grants-1979_01
Patent number
US04133827

Reaction notes

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