Sulfuric Acid → HCID 57422559, compound

HRID 913343Notes

Reaction equation

HRID 913343 reaction equation
Cl.[C:2]([C:10]1[CH:11]=[C:12]([C@H:16]([NH2:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.OS(O)(=O)=O.[S-:24][C:25]#[N:26].[Na+]>C1(C)C=CC=CC=1>[C:2]([C:10]1[CH:11]=[C:12]([C@H:16]([NH:18][C:25]([NH2:26])=[S:24])[CH3:17])[CH:13]=[CH:14][CH:15]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516871Sodium thiocyanateHCID 57462270HCID 57462270, compound

Product 1

HCID 57422559HCID 57422559, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (1R)-1-[(3-benzoyl)phenyl]ethylamine hydrochloride (0.52 g, 2 mmol) in toluene (15 mL), conc. H2SO4 (3 mmol) and sodium thiocyanate (0.18 g, 2.2 mmol) were added and the resulting mixture was left stirring at room temperature for 30 min. The formation of a white precipitate was observed: then the mixture was refluxed for 4 h and left stirring at room temperature overnight. The organic phase was washed with H2O (3×mL), dried over Na2SO4, filtered and evaporated under vacuum to give the N-[(1R)-1-(3-benzoylphenyl)ethyl]thiourea a dark red oil (0.53 g) pure enough (GC-Ms analysis) to be used without any further purification.

Workup

  1. waitthe resulting mixture was left
  2. temperaturethe mixture was refluxed for 4 h
  3. waitleft
  4. stirringstirring at room temperature overnight
  5. washThe organic phase was washed with H2O (3×mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-cfdf35dca6af4fe09deebff3313efb87
Source dataset
uspto-grants-2011_09
Patent number
US08026367B2

Reaction notes

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