Hypochlorous Acid → N-chloro-2-ethylhexyl carboxamide

HRID 1109267

Reaction equation

HRID 1109267 reaction equation
[CH2:1]([CH:3]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][C:5]([NH2:7])=[O:6])[CH3:2].[Cl:12]O>C(OCC)(=O)C>[Cl:12][NH:7][C:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:8][CH2:9][CH2:10][CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 24341Hypochlorous AcidHCID 126142952-Ethylhexyl carboxamide

Product 1

HCID 19022272N-chloro-2-ethylhexyl carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-ethylhexyl carboxamide (35.75 g, 250 mmol) was suspended in 300 ml of ethyl acetate and cooled to 1°. Hypochlorous acid (43.3 g of 30.6% solution, 252 m mol) was added dropwise over 13 minutes with stirring. After 10 minutes, the cooling bath was removed and stirring continued for 1 hour while the mixture warmed to room temperature. The ethyl acetate layer was then separated and dried (MgSO4) and the solvent was removed on the rotary evaporator and, finally, on the vacuum pump to give 44 g (98%) of colorless liquid N-chloro-2-ethylhexyl carboxamide.

Workup

  1. temperaturecooled to 1°
  2. customthe cooling bath was removed
  3. stirringstirring
  4. waitcontinued for 1 hour while the mixture
  5. customThe ethyl acetate layer was then separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed on the rotary evaporator

Sources & evidence

ORD record
ord-375172837e9046319c78f51387520bbe
Source dataset
uspto-grants-1994_06
Patent number
US05319133

Linked notes

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