Ammonium Chloride → S-2-amino-4-benzylphenyl dimethylcarbamothioate

HRID 2075253Notes

Reaction equation

HRID 2075253 reaction equation
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[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[N+:18]([O-])=O.[Cl-].[NH4+]>[Zn].CC(C)=O.O>[CH3:22][N:2]([CH3:1])[C:3](=[O:21])[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 2

HCID 25517Ammonium ChlorideHCID 58415382S-4-benzyl-2-nitrophenyl dimethylcarbamothioate

Product 1

HCID 58415349S-2-amino-4-benzylphenyl dimethylcarbamothioate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of S-4-benzyl-2-nitrophenyl dimethylcarbamothioate (1.58 g, 4.99 mmol) in 25 mL 5:1 acetone/water under nitrogen was added zinc, nanosize activated powder (1.63 g, 25.0 mmol) and ammonium chloride (2.67 g, 49.9 mmol). The reaction became hot and was cooled with an ice bath. The heterogeneous reaction was allowed to stir for ˜4 h. The reaction was allowed to stand overnight and was partitioned between 200 mL EtOAc and water. The organic layer was washed with brine, and dried over sodium sulfate, filtered, and concentrated to give S-2-amino-4-benzylphenyl dimethylcarbamothioate which was used without further purification. MS (ESI) m/z: Calculated: 286.1; Observed: 287.0 (M++1).

Workup

  1. temperaturewas cooled with an ice bath
  2. customThe heterogeneous reaction
  3. waitto stand overnight
  4. customwas partitioned between 200 mL EtOAc and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-21ca703908554a9bba1d5b2028f8cbc3
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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