Methyl iodide → HCID 12458615, compound

HRID 1390883Notes

Reaction equation

HRID 1390883 reaction equation
[NH2:1][CH2:2][CH3:3].Cl.[C:5]([NH:9][SH:10](=[O:12])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.[C:20](=[S:22])=[S:21].[CH3:23]I>C(O)C>[C:5]([NH:9][S:10]([CH2:3][CH2:2][NH:1][C:20](=[S:22])[S:21][CH3:23])(=[O:12])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 178449958HCID 178449958, compound

Product 1

HCID 12458615HCID 12458615, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Aminoethane-N-t-butylsulfonamide hydrochloride (1.25 g., 5.78 mmol.) was added to a solution of 1.17 g. (11.56 mmol.) of triethylamine in 20 ml. of ethanol. Carbon disulfide (0.44 g., 5.78 mmol.) was added, the mixture was stirred at 25° for 1.5 hours, then 0.82 g. (5.78 mmol.) of methyl iodide in 5 ml. of ethanol was added and the resulting mixture was stirred for 1.5 hours. The mixture was evaporated to dryness and the residue was dissolved in water and acidified to pH 2.0 with dilute hydrochloric acid. The aqueous mixture was extracted with ethyl acetate and the extract was dried (MgSO4) and evaporated to dryness to give methyl 2-(N-t-butylsulfamoyl)ethyldithiocarbamate.

Workup

  1. stirringthe resulting mixture was stirred for 1.5 hours
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in water
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a6eeba77cf794c0bb154adabf7e83481
Source dataset
uspto-grants-1979_02
Patent number
US04140694

Reaction notes

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