Isopropanol → N-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acid imide

HRID 1651484Notes

Reaction equation

HRID 1651484 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([CH3:19])[C:13]1=[O:20].[CH:21]([OH:24])([CH3:23])[CH3:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([O:24][CH:21]([CH3:23])[CH3:22])=[O:10])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([CH3:19])[C:13]1=[O:20]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 17802075N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acid imide

Product 1

HCID 17802081N-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acid imide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6 g of N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acid imide are added dropwise, while stirring at room temperature, to a mixture of 4 ml of isopropanol, 4 ml of triethylamine and 100 ml of toluene. After a reaction time of 6 hours, the triethylamine hydrochloride is separated off by filtration and the filtrate is concentrated by evaporation. By recrystallising the residue from ethanol/water, 4.2 g of N-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acid imide having a melting point of 161°-162° are obtained.

Workup

  1. customAfter a reaction time of 6 hours, the triethylamine hydrochloride is separated off by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. customBy recrystallising the residue from ethanol/water, 4.2 g of N-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acid imide having a melting point of 161°-162°
  4. customare obtained

Sources & evidence

ORD record
ord-6e5efd78d58641b592af41d8d6a262d5
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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