Water → HCID 178457773, compound

HRID 1380571Notes

Reaction equation

HRID 1380571 reaction equation
[Cl:1][C:2]1=[C:3]([Cl:9])[C:4]([O:6][C:7]1=[O:8])=[O:5].[CH3:10][CH:11]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)[CH2:12][NH2:13].O>C(O)(=O)C>[CH3:10][CH:11]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:22])([CH3:24])[CH3:23])=[CH:19][CH:20]=1)[CH2:12][N:13]=[C:4]([OH:5])/[C:3](/[Cl:9])=[C:2](/[Cl:1])\[C:7]([OH:6])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 70728Dichloromaleic anhydrideHCID 132903003-(4-tert-Butylphenyl)-2-methylpropan-1-amine

Product 1

HCID 178457773HCID 178457773, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.7 g (0.1 mol) of dichloromaleic anhydride and 20.5 g (0.1 mol) of 2-methyl-3-(4-tert.-butylphenyl)-propylamine are stirred in 100 ml of glacial acetic acid under reflux for 4 hours. 100 ml of water are added, the oil which has separated out is extracted with methylene chloride, the methylene chloride phase is concentrated and the residue is recrystallized from ethanol. 14.6 g (41.2% of theory) of dichloromaleic acid N-[2-methyl-3-(4-tert.-butylphenyl)-propyl]-imide of melting point 64°-65° C. are obtained.

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe oil which has separated out
  3. extractionis extracted with methylene chloride
  4. concentrationthe methylene chloride phase is concentrated
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-0757c7d5569f4122929dde6c4dc20450
Source dataset
uspto-grants-1986_04
Patent number
US04582849

Reaction notes

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