Chlorine → N-chloropelargonamide

HRID 2049522Notes

Reaction equation

HRID 2049522 reaction equation
[Cl:1]Cl.[C:3]([NH2:13])(=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>O>[Cl:1][NH:13][C:3](=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 70709Nonanamide

Product 1

HCID 10877964N-chloropelargonamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Gaseous chlorine is introduced at a speed of 95 g/h into a suspension of 194 g of 98.15% pure pelargonamide (1.21 mol) in 1400 ml of water. The introduction of chlorine is discontinued after 60 min and the suspension is still left under stirring for 20-30 min at 20° C. The solid is filtered off, is washed with water until all HCl has disappeared (300 cc. of water) and the chlorinated derivative is dried. 226 g of N-chloropelargonamide (yield 97.4%) having an active chlorine titer of 17.6% (theory 18.5%) are thus obtained.

Workup

  1. waitthe suspension is still left
  2. filtrationThe solid is filtered off
  3. washis washed with water until all HCl
  4. customthe chlorinated derivative is dried

Sources & evidence

ORD record
ord-0e7fc9dacb5444ee82c433c31a785ac3
Source dataset
uspto-grants-1980_04
Patent number
US04198348

Reaction notes

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