Hydrochloric Acid → HCID 23069070, compound

HRID 1373456Notes

Reaction equation

HRID 1373456 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.S(OCC)(OCC)(=O)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30].Cl.[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClC1C=CC=CC=1>[C:33]1([NH:32][C:1](=[O:7])/[CH:2]=[CH:3]/[C:4]([C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[C:24]([O:29][CH3:30])[CH:25]=2)=[O:5])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 6163Diethyl SulfateHCID 7043VeratroleHCID 7923Maleic AnhydrideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 23069070HCID 23069070, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
10 °C

Procedure

Into a 500 ml four-neck flask were charged 66.9 g (0.682 mol) of maleic anhydride, 150 ml of chlorobenzene, and 71.6 ml (0.546 mol) of diethyl sulfate under a nitrogen atmosphere. Then, the whole was cooled to 10° C. or lower and 67.6 g (0.507 mol) of aluminum chloride was added thereto. While temperature was maintained at 10 to 15° C., 25 ml (0.195 mol) of 1,2-dimethoxybenzene was added dropwise, followed by 4 hours of reaction. After termination of the reaction was confirmed by HPLC analysis, the reaction solution was added dropwise to 200 ml of a 1N hydrochloric acid aqueous solution cooled to 0° C. to decompose excess aluminum chloride. After liquid separation, the organic layer was washed with 200 ml of a 10% sodium bicarbonate aqueous solution to remove excess maleic anhydride. Then, 13.3 g (0.143 mol) of aniline was added, followed by 4 hours of refluxing while removing ethanol formed during the reaction. After completion of the reaction, the solvent was removed under reduced pressure and the residue was crystallized from 10 ml of ethanol to obtain 34.8 g (yield 57.4%) of the aimed compound. As a result of HPLC analysis, the purity was found to be 99.0%.

Workup

  1. temperatureWhile temperature was maintained at 10 to 15° C.
  2. customfollowed by 4 hours of reaction
  3. temperaturecooled to 0° C.
  4. customAfter liquid separation
  5. washthe organic layer was washed with 200 ml of a 10% sodium bicarbonate aqueous solution
  6. customto remove excess maleic anhydride
  7. temperatureof refluxing
  8. customwhile removing ethanol
  9. customformed during the reaction
  10. customAfter completion of the reaction
  11. customthe solvent was removed under reduced pressure
  12. customthe residue was crystallized from 10 ml of ethanol

Sources & evidence

ORD record
ord-27be1dc91c724295af21cfc1914d657b
Source dataset
uspto-grants-2007_01
Patent number
US07161022B2

Reaction notes

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