(3-Chlorophenyl)hydrazine → HCID 178478162, compound

HRID 1578359Notes

Reaction equation

HRID 1578359 reaction equation
[C:1]1(O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=1.COC.[Cl:12][C:13]1[CH:14]=[C:15]([NH:19][NH2:20])[CH:16]=[CH:17][CH:18]=1>C(O)(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([NH:19][N:20]=[C:1]2[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 75332(3-Chlorophenyl)hydrazineHCID 178499087HCID 178499087, compound

Product 1

HCID 178478162HCID 178478162, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

35 G (0.28 mole) of caprolactim-methyl-ether were added dropwise over the course of 15 minutes at 5°C, while stirring and cooling, to a solution of 36 g (0.25 mole) of 3-chlorophenylhydrazine in 250 ml of glacial acetic acid; the red-brown clear solution was kept at 0° to 5°C for a further 2 hours and then for 2 hours at 20°C and excess glacial acetic acid was distilled off in a water-pump vacuum. On fractional distillation in vacuo of the residue which remained, 56 g (94.3% of theory) of caprolactam-(3-chlorophenylhydrazone) were obtained; it was a light viscous oil of boiling point 215° to 220°C/3 mmHg, which solidified to crystals.

Workup

  1. waitfor 2 hours at 20°C
  2. distillationexcess glacial acetic acid was distilled off in a water-pump vacuum
  3. distillationOn fractional distillation in vacuo of the residue which

Sources & evidence

ORD record
ord-501dceeaf17e41fa9a686057bbd6c72d
Source dataset
uspto-grants-1976_02
Patent number
US03936444

Reaction notes

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