Acetyl chloride → Methyl-N-acetyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate

HRID 2253669Notes

Reaction equation

HRID 2253669 reaction equation
I.[CH3:2][S:3][C:4]([N:6]([CH3:15])[N:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[NH:5].C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[CH3:2][S:3][C:4]([N:6]([CH3:15])[N:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N:5][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70433894Methyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate-hydroiodide

Product 1

HCID 54432660Methyl-N-acetyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate-hydroiodide* (4 g) and triethylamine (2.5 g) were dissolved in dichloromethane (50 ml). To this solution acetyl chloride (1.05 g) was added slowly maintaining temperature below 20° C. The mixture was stirred at room temperature in a dry nitrogen atmosphere for 1.5 h. The organic residues were washed with water (5×20 ml), dried over anhydrous sodium sulphate and the solvent removed in vacuo giving a yellow solid which upon trituration with ether gave the title compound (2.30 g) as an off-white solid of m.pt. 102°-104° C.

Workup

  1. temperaturemaintaining temperature below 20° C
  2. washThe organic residues were washed with water (5×20 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvent removed in vacuo
  5. customgiving a yellow solid which upon trituration with ether

Sources & evidence

ORD record
ord-405d644f544b4767ab2ea47b264b90cb
Source dataset
uspto-grants-1993_08
Patent number
US05232938

Reaction notes

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