Dimethylmaleic anhydride → HCID 17802073, compound

HRID 1651487Notes

Reaction equation

HRID 1651487 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:5][C:3]=1[NH2:4].[CH3:14][C:15]1=[C:16]([CH3:22])[C:17]([O:19][C:20]1=O)=[O:18]>C(O)(=O)C>[Cl:9][C:7]1[C:6]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:5][C:3]([N:4]2[C:17](=[O:18])[C:16]([CH3:22])=[C:15]([CH3:14])[C:20]2=[O:19])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-

Product 1

HCID 17802073HCID 17802073, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20.4 g (0.1 mol) of 2-fluoro-4-chloro-5-isopropoxyaniline and 12.6 g (0.1 mol) of dimethylmaleic anhydride in 100 ml of glacial acetic acid is stirred for 6 hours at a temperature of 130°-140°. It is then allowed to cool to room temperature and the almost black reaction solution is concentrated in a rotary evaporator. The residue is taken up in ethyl acetate and the solution is washed in succession with water, 1M soda solution, water and concentrated salt brine. It is then dried over sodium sulphate, filtered and concentrated in vacuo. The dark oil remaining is crystallised from ethanol with the aid of activated carbon. 17.6 g of title product (56.5% of the theoretical yield) which melts at 93°-95° is thus obtained.

Workup

  1. concentrationthe almost black reaction solution is concentrated in a rotary evaporator
  2. washthe solution is washed in succession with water, 1M soda solution, water and concentrated salt brine
  3. dry with materialIt is then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe dark oil remaining is crystallised from ethanol with the aid of activated carbon

Sources & evidence

ORD record
ord-894a529f889a4f9fb00025db4dd736ab
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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