p-Toluenesulfonic acid monohydrate → HCID 14502061, compound

HRID 231867Notes

Reaction equation

HRID 231867 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[O:11]1.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]2[NH:1][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:10]([O:11][CH3:21])[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14502060HCID 14502060, compound

Product 1

HCID 14502061HCID 14502061, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 300 ml of methyl alcohol was dissolved 22.45 g of 3-(2-amino-3, 5-dimethylphenyl)-1, 3-dihydroisobenzofuran-1-one. The solution was heated at reflux for 10 hours in the presence of 20.23 g of p-toluenesulfonic acid monohydrate. The resulting solution was concentrated to dryness under reduced pressure. The obtained solid was dissolved in 200 ml of dichloromethane. The solution was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the solution was filtered and the resulting filtrate was concentrated to dryness under reduced pressure. To the obtained solid was added to diisopropyl ether and the solid was ground into powders. Thus, 12.65 g of 2,4-dimethyl-11-methoxy-5, 11-dihydro-6H-dibenz[b,e]azepin-6-one was obtained.

Workup

  1. temperatureThe solution was heated
  2. concentrationThe resulting solution was concentrated to dryness under reduced pressure
  3. dissolutionThe obtained solid was dissolved in 200 ml of dichloromethane
  4. washThe solution was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. filtrationthe solution was filtered
  7. concentrationthe resulting filtrate was concentrated to dryness under reduced pressure
  8. additionTo the obtained solid was added to diisopropyl ether

Sources & evidence

ORD record
ord-fba7940cd16b4887ba9d875ed6bb9aa2
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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