Methyl iodide → Methyl 2-acetamidoethyldithiocarbamate

HRID 839595Notes

Reaction equation

HRID 839595 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 was 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
  7. extractionThe aqueous solution was extracted twice with 250 ml
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-f77a2c464d3e480bb4cf1f5ecb8a5d7e
Source dataset
uspto-grants-1978_06
Patent number
US04096256

Reaction notes

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