Acetic Acid → 3,4-Dichlorophenylcyanamide

HRID 414394Notes

Reaction equation

HRID 414394 reaction equation
[N:1]#[C:2]Cl.[Cl:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[Cl:12])[NH2:8].C(O)(=O)C.[OH-].[Na+]>C(O)C>[Cl:4][C:5]1[CH:6]=[C:7]([NH:8][C:2]#[N:1])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 72573,4-DichloroanilineHCID 10477Cyanogen ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 6042543,4-DichlorophenylcyanamideYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.1 ml (0.12 mole) of cyanogen chloride were added, at a temperature below 10° C., to 16.3 g (0.1 mole) of 3,4-dichloroaniline in 150 ml of ethanol and 40 g of 50% strength acetic acid. 110 ml of 1N NaOH solution was then added dropwise. The mixture was stirred for a further hour and concentrated under a water pump vacuum until a bath temperature of 30° C. had been reached, and the residue was washed with water. 17.8 g (≅95% of theory) of 3,4-dichlorophenyl cyanamide were obtained. The substance was homogeneous according to examination by thin layer chromatography and gave a clear solution in 2N NaOH.

Workup

  1. concentrationconcentrated under a water pump vacuum until a bath temperature of 30° C.
  2. washthe residue was washed with water

Sources & evidence

ORD record
ord-adb37c39c51a451b82a8f73779977861
Source dataset
uspto-grants-1988_12
Patent number
US04791229

Reaction notes

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