Hypochlorous Acid → N-chloro-2-methyl decanamide

HRID 1109275Notes

Reaction equation

HRID 1109275 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([NH2:5])=[O:4].O[Cl:15]>C(Cl)Cl>[Cl:15][NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 24341Hypochlorous AcidHCID 179174482-Methyldecanoic acid amide

Product 1

HCID 54088766N-chloro-2-methyl decanamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2 °C

Procedure

2-Methyl decanamide (50 g, 270 mmol) was suspended in 300 ml of methylene chloride, cooled to 2° C. and aqueous HOCl (14.72 g, 280 mmol) was added over about 10 minutes. The mixture was stirred in the cold for 15 minutes, then at room temperature for 45 minutes. The methylene chloride layer was separated, dried over magnesium sulfate, and the solvent removed on a rotary evaporator in a warm water bath to give 56 g (94% yield) of white solid product, m.p. 56°-57° C.

Workup

  1. waitat room temperature for 45 minutes
  2. customThe methylene chloride layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed on a rotary evaporator in a warm water bath

Sources & evidence

ORD record
ord-3d6293931b19480687f6bc2e970b2375
Source dataset
uspto-grants-1994_06
Patent number
US05319133

Reaction notes

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