Methyl iodide → Methyl 2-acetamidoethyldithiocarbamate

HRID 426749

Reaction equation

HRID 426749 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:7])[CH3:6].C(N(CC)CC)C.[C:15](=[S:17])=[S:16].[CH3:18]I>C(O)C>[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:15](=[S:17])[S:16][CH3:18])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamide

Product 1

HCID 20501582Methyl 2-acetamidoethyldithiocarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20.4 g (0.20 mol) of N-(2-aminoethyl)acetamide in 200 ml of 95% ethanol was added 27.9 ml (0.20 mol) of triethylamine and 12.0 ml (0.20 mol) of carbon disulfide. The exothermic reaction reached reflux and then cooled to ambient temperature over a 1.5 hour period. Methyl iodide (28.4 g, 0.20 mol) was added which again produced an exothermic reaction. After 1.75 hours the reaction mixture was evaporated to dryness and the solid residue was dissolved in 200 ml of water. The aqueous solution was extracted twice with 250 ml portions of ethyl acetate. The extracts were combined, shaken with sodium thiosulfate, dried (MgSO4) and evaporated to dryness to give methyl 2-acetamidoethyldithiocarbamate.

Workup

  1. customThe exothermic reaction
  2. temperaturereached reflux
  3. customagain produced
  4. customan exothermic reaction
  5. customAfter 1.75 hours the reaction mixture was evaporated to dryness
  6. dissolutionthe solid residue was dissolved in 200 ml of water
  7. extractionThe aqueous solution was extracted twice with 250 ml portions of ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ba032167005c46fba3dc68558cc03c60
Source dataset
uspto-grants-1979_10
Patent number
US04171368

Linked notes

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