Water → 2-(2-(2-Amino-4-benzylphenyl)disulfanyl)-5-benzylbenzenamine

HRID 2075254Notes

Reaction equation

HRID 2075254 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[NH2:18].[OH-].[K+].O>C(O)CO>[NH2:18][C:6]1[CH:7]=[C:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][C:5]=1[S:4][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][C:6]=1[NH2:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58415349S-2-amino-4-benzylphenyl dimethylcarbamothioate

Product 1

HCID 584152952-(2-(2-Amino-4-benzylphenyl)disulfanyl)-5-benzylbenzenamine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
60 °C

Procedure

To a slurry of S-2-amino-4-benzylphenyl dimethylcarbamothioate (1.43 g, 4.99 mmol) in 15 mL ethylene glycol was added potassium hydroxide (0.840 g, 15.0 mmol) (solid, finely crushed). The reaction was heated to 60° C. under nitrogen. 10 mL 2-BuOH was added as cosolvent and the resulting solution was heated for 2 h. The reaction was fitted with a water-cooled reflux condensor and heated to 90° C. for 3 h. The reaction was cooled, and concentrated in vacuo. The material was partitioned between Et2O and water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give an oil, which was purified by silica gel chromatography, ISCO, 0-30% EtOAc/hexanes to give 2-(2-(2-amino-4-benzylphenyl)disulfanyl)-5-benzylbenzenamine as a brown oil. MS (ESI) m/z: Calculated: 428.1; Observed: 429.0 (M++1).

Workup

  1. customfinely crushed)
  2. temperaturethe resulting solution was heated for 2 h
  3. temperaturecooled
  4. temperaturereflux condensor
  5. temperatureheated to 90° C. for 3 h
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated in vacuo
  8. customThe material was partitioned between Et2O and water
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give an oil, which
  13. customwas purified by silica gel chromatography, ISCO, 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-85536e841b4a4a689bf79a9da63eb445
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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