Methylamine → Methyl[(1,1,2,2-tetrachloroethyl)sulfanyl]carbamyl chloride

HRID 597383Notes

Reaction equation

HRID 597383 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[Cl:10][C:11]([Cl:17])([S:15]Cl)[CH:12]([Cl:14])[Cl:13].[C:18]([Cl:21])(Cl)=[O:19]>C(#N)C>[Cl:10][C:11]([S:15][N:5]([CH3:3])[C:18]([Cl:21])=[O:19])([Cl:17])[CH:12]([Cl:14])[Cl:13]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 144531,1,2,2-Tetrachloroethylsulfenyl chloride

Product 1

HCID 21447651Methyl[(1,1,2,2-tetrachloroethyl)sulfanyl]carbamyl chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3.1 g (0.1 mole) methylamine and 10.1 g (0.1 mole) triethylamine in 100 ml acetonitrile was added dropwise to a solution of 23.4 g (0.1 mole) 1,1,2,2-tetrachloroethylsulfenyl chloride in 200 ml acetonitrile at about 0°-5° C. Into the reaction mixture was then bubbled 9.9 g (0.1 mole) phosgene. The reaction was stirred at about 25° C for about 17 hours. The acetonitrile solvent was evaporated under reduced pressure and the residue was diluted with benzene and filtered to give a filtrate solution of N-1,1,2,2-tetrachloroethylthio N-methyl carbamoyl chloride in benzene.

Workup

  1. customThe acetonitrile solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with benzene
  3. filtrationfiltered

Sources & evidence

ORD record
ord-48c25e8f208a46e2955c37aeb2536e9a
Source dataset
uspto-grants-1977_03
Patent number
US04013774

Reaction notes

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