Water → chloromaleic acid N-[2-(2-methoxyphenyl)-ethyl]-imide

HRID 979228

Reaction equation

HRID 979228 reaction equation
[Cl:1][C:2]1[C:3]([O:5][C:6](=[O:8])[CH:7]=1)=[O:4].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][NH2:19].O>C(O)(=O)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][N:19]=[C:3]([OH:4])/[C:2](/[Cl:1])=[CH:7]\[C:6]([OH:5])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 66772Chloromaleic anhydrideHCID 748962-Methoxyphenethylamine

Product 1

HCID 178489456chloromaleic acid N-[2-(2-methoxyphenyl)-ethyl]-imideYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

13.25 g (0.1 mol) of chloromaleic anhydride and 15.2 g (0.1 mol) of 2-(2-methoxyphenyl)-ethylamine are heated to the boiling point in 100 ml of glacial acetic acid for 4 hours. 100 ml of water are then added and the oil which has precipitated is extracted with methylene chloride. The methylene chloride phase is separated off, washed with water, dried and evaporated. The oil which remains crystallizes. 20.8 g (78% of theory) of chloromaleic acid N-[2-(2-methoxyphenyl)-ethyl]-imide are obtained.

Workup

  1. customthe oil which has precipitated
  2. extractionis extracted with methylene chloride
  3. customThe methylene chloride phase is separated off
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe oil which remains crystallizes

Sources & evidence

ORD record
ord-33887f723c6e4b00a2adcfa2a364aa5b
Source dataset
uspto-grants-1987_05
Patent number
US04666935

Linked notes

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