2-(Methylsulfanyl)acetyl chloride → Methyl N-[2-(methylthio)acetyl]-1-methyl-2-(phenylmethylene)hydrazine carboximidothioate

HRID 652086Notes

Reaction equation

HRID 652086 reaction equation
[CH3:1][S:2][CH2:3][C:4](Cl)=[O:5].I.[CH3:8][N:9]([C:18]([S:20][CH3:21])=[NH:19])[N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(N(CC)CC)C.ClCCl>[CH3:1][S:2][CH2:3][C:4]([N:19]=[C:18]([N:9]([CH3:8])[N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[S:20][CH3:21])=[O:5]

Participants

5

Reactant 2

HCID 111262562-(Methylsulfanyl)acetyl chlorideHCID 70433894Methyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate-hydroiodide

Product 1

HCID 53810570Methyl N-[2-(methylthio)acetyl]-1-methyl-2-(phenylmethylene)hydrazine carboximidothioateYield 50.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

(Methylthio)acetyl chloride (5.6 g) was added portionwise to a solution of methyl 1-methyl-2-(phenylmethylene)hydrazine carboximidothioate hydroiodide (A) (10.4 g) in triethylamine (7.08 g) and dichloromethane (55 ml) and the mixture stirred at room temperature for 2 h. The mixture was washed with water and evaporated to give an oil which was chromatographed using 1:1 ether-petroleum ether (b.p. 60°-80°) followed by ether to give the title compound (4.6 g) as a cream solid, m.p. 68°-70°.

Workup

  1. washThe mixture was washed with water
  2. customevaporated
  3. customto give an oil which
  4. customwas chromatographed

Sources & evidence

ORD record
ord-42f22c7db98546cebedc4d33a6b521ea
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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