Methyl iodide → Methyl 2-acetamidoethyldithiocarbamate

HRID 866876

Reaction equation

HRID 866876 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 then added which again produced an exothermic reaction. After an additional 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 solid 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 an additional 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-7a65c47ef51f4ba681707a32a457aae0
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Linked notes

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