Acetone → HCID 178435013, compound

HRID 1729977Notes

Reaction equation

HRID 1729977 reaction equation
CC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O:18][C:19]1([CH3:34])[C:23]2=[N+:24]([O-:33])[C:25]3[C:30]([N+:31]([O-:32])=[C:22]2[CH2:21][O:20]1)=[CH:29][CH:28]=[CH:27][CH:26]=3>O>[OH:18][C:19]1([CH3:34])[C:23]2=[N+:24]([O-:33])[C:25]3[C:30]([N+:31]([O-:32])=[C:22]2[CH2:21][O:20]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 178493816HCID 178493816, compound

Product 1

HCID 178435013HCID 178435013, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1,500 ml. of acetone and 75 ml. of water, containing 3.78 g. (0.02 mol.) of 4-toluenesulfonic acid monohydrate, was added 63.6 g. (0.26 mol.) of 1-methoxy-1-methyl-1,3-dihydrofuro[3,4-b]quinoxaline 4,9-dioxide. The reaction mixture was heated under reflux for 4.5 hours and then allowed to cool to ambient temperature. The solvent was removed by evaporation in vacuo, and the residue was washed with ether. This afforded 58.7 g. (98% yield) of crude product. The crude product was recrystallized from water with the aid of activated carbon, to give a 68% yield of product having m.p. 159°-160° C.

Workup

  1. additionTo a mixture of 1,500 ml
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 4.5 hours
  4. customThe solvent was removed by evaporation in vacuo
  5. washthe residue was washed with ether
  6. customThe crude product was recrystallized from water with the aid of activated carbon

Sources & evidence

ORD record
ord-cafd9dd19a9541a48d41a3dc29c79ca5
Source dataset
uspto-grants-1976_11
Patent number
US03991053

Reaction notes

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