Water → HCID 178446582, compound

HRID 1380568Notes

Reaction equation

HRID 1380568 reaction equation
[Cl:1][C:2]1=[C:3]([Cl:9])[C:4]([O:6][C:7]1=[O:8])=[O:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][NH2:19])=[CH:13][CH:12]=1.O>C(O)(=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][N:19]=[C:4]([OH:5])/[C:3](/[Cl:9])=[C:2](/[Cl:1])\[C:7]([OH:6])=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70728Dichloromaleic anhydrideHCID 13290298HCID 13290298, compound

Product 1

HCID 178446582HCID 178446582, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

16.7 g (0.1 mol) of dichloromaleic anhydride and 19.7 g (0.1 mol) of 2-(4-chlorophenyl)-3-methylbutylamine are stirred in 100 ml 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. 21.2 g of dichloromaleic acid N-[2-(4-chlorophenyl)-3-methylbutyl]imide of melting point 91°-92° C. are obtained. A further 10.4 g of imide can also be isolated by stirring the mother liquor with water. The total yield is: 91.3% of theory.

Workup

  1. filtrationis filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-f524a0bc58bb48779f2deb079ba23eab
Source dataset
uspto-grants-1986_04
Patent number
US04582849

Reaction notes

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