Methyl iodide → Methyl (3-acetamidopropyl)carbamodithioate

HRID 543835Notes

Reaction equation

HRID 543835 reaction equation
N[CH2:2]CCNC(=O)C.[OH-].[Na+].[C:11]([NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[S:21])[S-:20])(=[O:13])[CH3:12].[Na+].CI>O1CCOCC1.O.C(=S)=S>[C:11]([NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[S:20])[S:21][CH3:2])(=[O:13])[CH3:12]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13793967N-(3-Aminopropyl)acetamideHCID 23674641HCID 23674641, compound

Product 1

HCID 23324174Methyl (3-acetamidopropyl)carbamodithioate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6348Carbon DisulfideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(3-aminopropyl)acetamide (146 g) in dioxane (710 ml) was added to a solution of 97% sodium hydroxide (52 g) in water (620 ml) and then carbon disulfide (96 g) was added dropwise thereto over 35 minutes at -1° to 3° C. The mixture was stirred for 1 hour at 0° to 2° C. To the mixture containing sodium N-(3-acetamidopropyl)dithiocarbamate was added dropwise methyl iodide (179 g) over 35 minutes at 0° to 5° C. and then the resulting mixture was stirred for 3 hours at the same temperature. Dioxane was distilled off in vacuo from the reaction mixture and the residue was extracted with ethyl acetate (300 ml, 200 ml×4). The extracts were dried over magnesium sulfate and concentrated in vacuo to give oil of methyl N-(3-acetamidopropyl)dithiocarbamate (193.18 g).

Workup

  1. stirringthe resulting mixture was stirred for 3 hours at the same temperature
  2. distillationDioxane was distilled off in vacuo from the reaction mixture
  3. extractionthe residue was extracted with ethyl acetate (300 ml, 200 ml×4)
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a89756f8a07c43f6a63eb90118f87ab6
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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