Ammonium Chloride → 2-Phenylethanethioamide

HRID 2120279Notes

Reaction equation

HRID 2120279 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+:11].[Cl-]>ClCCl>[C:1]1([CH2:7][C:8]([NH2:11])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 19906501Benzylthiocarbonyl chloride

Product 1

HCID 7313682-Phenylethanethioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of secondary amine I and TEA in anhydrous dichloromethane, are added dropwise a solution of phenylthioacetyl chloride (prepared from phenylthioacetic acid and thionyl chloride) in anhydrous dichloromethane at 0° C. The reaction mixture is warmed to room temperature, stirred for 2 hours, then sat'd NH4Cl solution and dichloromethane are added. The organic layer is washed with brine, dried over Na2SO4, and concentrated to afford α-phenylthioacetamide II, which is used for the next reaction without purification.

Workup

  1. additionare added
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e0c4256e4054aa6bcbfe1efa6f660b3
Source dataset
uspto-grants-2004_02
Patent number
US06689890B2

Reaction notes

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