Water → HCID 17802079, compound

HRID 1651486Notes

Reaction equation

HRID 1651486 reaction equation
[CH3:1][C:2]1=[C:3]([CH3:9])[C:4]([O:6][C:7]1=O)=[O:5].[F:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[NH2:13].O>CN(C)C1C=CN=CC=1.CC1C=CC=CC=1C>[F:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[N:13]1[C:7](=[O:6])[C:2]([CH3:1])=[C:3]([CH3:9])[C:4]1=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 13010Dimethylmaleic anhydrideHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 17802079HCID 17802079, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 126 g (1.0 mol) of dimethylmaleic anhydride, 145.5 g (1.0 mol) of 2-fluoro-4-chloroaniline and 2 g of 4-dimethylaminopyridine is heated under reflux in 800 ml of o-xylene for 16 hours using a water separator. The whole is then evaporated to dryness in vacuo and the residue is dissolved in a 1:1 mixture of ethyl acetate:ether and washed with each of 1N hydrochloric acid, 1N sodium hydroxide solution and water. After drying over sodium sulphate and evaporating off the solvent, the residue (227.5 g) is recrystallised from methanol. In this manner there are obtained 211.1 g (84% of the theoretical yield) of the title product in the form of colourless crystals which melt at 96°-97°.

Workup

  1. temperatureis heated
  2. customThe whole is then evaporated to dryness in vacuo
  3. dissolutionthe residue is dissolved in a 1:1 mixture of ethyl acetate
  4. washether and washed with each of 1N hydrochloric acid, 1N sodium hydroxide solution and water
  5. dry with materialAfter drying over sodium sulphate
  6. customevaporating off the solvent
  7. customthe residue (227.5 g) is recrystallised from methanol
  8. customIn this manner there are obtained 211.1 g (84% of the

Sources & evidence

ORD record
ord-0703adcfb71d474e88474e9c485ec15d
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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