Water → N-phenylthioanthranilic acid S-methyl ester

HRID 1722820Notes

Reaction equation

HRID 1722820 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Cl)(Cl)Cl.[CH3:18][S:19][C:20]#N.[OH2:22]>C1(C)C=CC=CC=1>[CH3:18][S:19][C:20](=[O:22])[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11168Methyl thiocyanateHCID 11487DiphenylamineHCID 25135Boron Trichloride

Product 1

HCID 14547556N-phenylthioanthranilic acid S-methyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1.69 g of diphenylamine in 10 ml of toluene was added 5.5 ml of a solution of 2.02M boron trichloride--toluene under ice-cooling, and the mixture was refluxed with heating on an oil bath for 1 hr. After ice-cooling, the reaction mixture was mixed with 1 ml of methyl thiocyanate and stirred at room temperature for 16 hr. The reaction mixture was mixed with 20 ml of water and refluxed with heating on an oil bath for 30 min. The insoluble materials were filtered off and the toluene layer was dried over anhydrous magnesium sulfate, chromatographed on a column of silica gel and eluted with toluene. The solvent was concentrated to give 1.03 g of N-phenylthioanthranilic acid S-methyl ester as a yellow oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating on an oil bath for 1 hr
  3. temperatureAfter ice-cooling
  4. temperaturerefluxed
  5. temperaturewith heating on an oil bath for 30 min
  6. filtrationThe insoluble materials were filtered off
  7. dry with materialthe toluene layer was dried over anhydrous magnesium sulfate
  8. customchromatographed on a column of silica gel
  9. washeluted with toluene
  10. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-85630bcfc920449592f0374055dd14d1
Source dataset
uspto-grants-1989_08
Patent number
US04857645

Reaction notes

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