2,5-Furandione, 3-ethyl-4-methyl- → HCID 57094154, compound

HRID 1381841Notes

Reaction equation

HRID 1381841 reaction equation
[CH2:1]([C:3]1[C:4]([O:6][C:7](=[O:10])[C:8]=1[CH3:9])=O)[CH3:2].[F:11][C:12]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:15][C:13]=1[NH2:14]>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[F:11][C:12]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]([CH3:22])[CH3:23])=[CH:15][C:13]=1[N:14]1[C:7](=[O:10])[C:8]([CH3:9])=[C:3]([CH2:1][CH3:2])[C:4]1=[O:6]

Participants

5

Reactant 2

HCID 770912,5-Furandione, 3-ethyl-4-methyl-HCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-

Product 1

HCID 57094154HCID 57094154, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

5 g of 2-ethyl-3-methylmaleic anhydride, 7.3 g of 2-fluoro-4-chloro-5-isopropoxyaniline and 0.61 g of 4-dimethylaminopyridine are combined in 100 ml of xylene in a distillation apparatus and the solvent is slowly distilled off. After 5 hours, the reaction is complete. The xylene still present is removed under a water-jet vacuum. The dark residue is taken up in ethyl acetate and extracted with 2M hydrochloric acid, water, 10% sodium bicarbonate solution and lastly with saturated sodium chloride solution. After drying over sodium sulphate, the ethyl acetate is distilled off in a rotary evaporator and the residue is chromatographed over a column of silica gel with hexane:ethyl acetate 1:1. After evaporating the solvent, 5 g of the title compound are obtained in the form of a red oil having a refractive index of nD22 =1.5351.

Workup

  1. distillationthe solvent is slowly distilled off
  2. customThe xylene still present is removed under a water-jet vacuum
  3. extractionextracted with 2M hydrochloric acid, water, 10% sodium bicarbonate solution and lastly with saturated sodium chloride solution
  4. dry with materialAfter drying over sodium sulphate
  5. distillationthe ethyl acetate is distilled off in a rotary evaporator
  6. customthe residue is chromatographed over a column of silica gel with hexane:ethyl acetate 1:1
  7. customAfter evaporating the solvent, 5 g of the title compound
  8. customare obtained in the form of a red oil

Sources & evidence

ORD record
ord-b7a198ae5d754f62981ba02fa8e04043
Source dataset
uspto-grants-1989_02
Patent number
US04804400

Reaction notes

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