Carbon Disulfide → N,N-dimethyl-5-[[[2-(isothiocyanato)ethyl]thio]methyl]furanmethanamine

HRID 1278010Notes

Reaction equation

HRID 1278010 reaction equation
[C:1](=S)=[S:2].[NH2:4][CH2:5][CH2:6][S:7][CH2:8][C:9]1[O:13][C:12]([CH2:14][N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>CC(C)=O>[N:4]([CH2:5][CH2:6][S:7][CH2:8][C:9]1[O:13][C:12]([CH2:14][N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 20513971N,N-dimethyl-5-[[[2-(isothiocyanato)ethyl]thio]methyl]furanmethanamineYield 39.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of carbon disulphide (4.2 g) in dry acetone (8 ml) was added dropwise to a solution of 5-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine (10.71 g) in dry acetone (30 ml) during 15 minutes at -10° to 0°. To the stirred solution at -15° was added dropwise a solution of mercuric chloride (13.6 g) in dry acetone (20 ml) during 45 minutes. The solution was warmed to 0° and triethylamine (11.5 g) was added dropwise with stirring during 15 minutes. The mixture was refluxed for 45 minutes, the suspension filtered and the filtrate evaporated to dryness. The oily residue was dissolved in ether (150 ml), decolourising charcoal and excess anhydrous sodium sulphate were added and the suspension filtered after 2 hours. The filtrate was evaporated to dryness, the oily residue dissolved in ether and the solution chromatographed (alumina deactivated with water, 72.5 ml/kg/ether). The appropriate eluate was evaporated to give the title compound (5.05 g) as a brown oil.

Workup

  1. temperatureThe solution was warmed to 0°
  2. temperatureThe mixture was refluxed for 45 minutes
  3. filtrationthe suspension filtered
  4. customthe filtrate evaporated to dryness
  5. dissolutionThe oily residue was dissolved in ether (150 ml)
  6. additionwere added
  7. filtrationthe suspension filtered after 2 hours
  8. customThe filtrate was evaporated to dryness
  9. dissolutionthe oily residue dissolved in ether
  10. customthe solution chromatographed (alumina deactivated with water, 72.5 ml/kg/ether)
  11. customThe appropriate eluate was evaporated

Sources & evidence

ORD record
ord-5b99c61f2d9c47adbd6533900326bb0a
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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