Water → HCID 178525579, compound

HRID 979226Notes

Reaction equation

HRID 979226 reaction equation
[Cl:1][C:2]1=[C:3]([Cl:9])[C:4]([O:6][C:7]1=[O:8])=[O:5].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH2:19])=[CH:13][CH:12]=1.O>C(O)(=O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][N:19]=[C:4]([OH:5])/[C:3](/[Cl:9])=[C:2](/[Cl:1])\[C:7]([OH:6])=[O:8])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4653p-FluorophenethylamineHCID 70728Dichloromaleic anhydride

Product 1

HCID 178525579HCID 178525579, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

16.7 g (0.1 mol) of dichloromaleic anhydride and 14.0 g (0.1 mol) of 2-(4-fluorophenyl)-ethylamine are stirred in 100 ml of glacial acetic acid at 120° C. for 4 hours. The mixture is cooled to 20° C. and 10 ml of water are added. A colorless precipitate separates out, and is filtered off with suction and dried. 16 g of dichloromaleic acid N-[2-(4-fluorophenyl)-ethyl]-imide of melting point 137°-138° C. are obtained. A further 5.1 g of imide can be isolated by stirring the mother liquor with water. The total yield is 73% of theory.

Workup

  1. filtrationis filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-f4ea6c416cd149d1ac463d7566700e53
Source dataset
uspto-grants-1987_05
Patent number
US04666935

Reaction notes

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