Hydrochloric Acid → HCID 53815997, compound

HRID 892427Notes

Reaction equation

HRID 892427 reaction equation
C([CH:3]([C:14]([NH2:16])=[O:15])[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])C.[CH2:17](N)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C)C=O.Cl>C1(C)C=CC=CC=1>[CH2:17]([NH:16][C:14](=[O:15])[CH2:3][C:4]([NH:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8143OctylamineHCID 13520966HCID 13520966, compound

Product 1

HCID 53815997HCID 53815997, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.1 g (5.0 mol) of ethyl N-benzylmalonamide in 30 mL of toluene was heated to reflux under nitrogen and 1.29 g (10.0 mol) of n-octylamine was added. The reaction was heated to reflux for 5 h and 5 mL of N,N-dimethylformamide was added. This mixture was kept at reflux for 12 h and poured into 5% aqueous hydrochloric acid. the organic layer was washed with saturated aqueous sodium bicarbonate, water, brine, and dried over magnesium sulfate. Filtration and removal of solvents afforded a crude solid which was recrystallized from 50% ethyl acetate/hexane to give 0.8 g (53% yield) of N-n-octyl-N'-benzylmalonamide.

Workup

  1. temperatureto reflux under nitrogen
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 5 h
  4. temperatureat reflux for 12 h
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate, water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and removal of solvents
  8. customafforded a crude solid which
  9. customwas recrystallized from 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4c3e78ecfb044840a788f97de259b4f2
Source dataset
uspto-grants-1992_06
Patent number
US05118681

Reaction notes

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