3,4-Dichloroaniline → 3,4-Dichlorophenylcyanamide

HRID 414393Notes

Reaction equation

HRID 414393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[N:10]#[C:11]Cl.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]#[N:10])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

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

Product 1

HCID 6042543,4-DichlorophenylcyanamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.2 g (0.1 mole) of 3,4-dichloroaniline were dissolved in 278 g of 64% strength acetic acid; 6.1 ml (0.12 mole) of cyanogen chloride were added at 10° C. and 22 g (0.11 mole) of 20% strength NaOH solution were then added dropwise slowly, with stirring. The mixture was stirred for a further 2 hours at room temperature and filtered with suction, and the filter residue was washed with water and dried. This gave 15 g (≅80% of theory) of 3,4-dichlorophenyl cyanamide which gave a clear solution in 2N NaOH and was homogeneous according to examination by thin layer chromatography.

Workup

  1. stirringThe mixture was stirred for a further 2 hours at room temperature
  2. filtrationfiltered with suction
  3. washthe filter residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-023b5e767a0f4397b110f61898e0c163
Source dataset
uspto-grants-1988_12
Patent number
US04791229

Reaction notes

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