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

HRID 426501Notes

Reaction equation

HRID 426501 reaction equation
[C:1](=[S:3])=S.[OH-].[Na+].[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15][S:16][CH2:17][CH2:18][NH2:19])=[CH:12][CH:11]=1)[CH3:8].ClC(OCC)=O>O>[CH3:6][N:7]([CH3:8])[CH2:9][C:10]1[O:14][C:13]([CH2:15][S:16][CH2:17][CH2:18][N:19]=[C:1]=[S:3])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Carbon disulphide (1.52 g) was added with stirring to a cooled solution of sodium hydroxide (0.8 g) in water (1.7 ml). 2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (4.26 g) was added slowly and when addition was complete the mixture heated at 100° for 2 hr. After cooling to below 40° ethyl chloroformate (1.94 ml) was added and stirring continued for a further 30 mins. The lower thick yellow oil was extracted with chloroform, dried and evaporated to give N,N-dimethyl-5-[[[2-(isothiocyanato)ethyl]thio]methyl]furanmethanamine as an oil RF 0.43 (silica/methanol).

Workup

  1. additionwhen addition
  2. temperatureheated at 100° for 2 hr
  3. additionwas added
  4. extractionThe lower thick yellow oil was extracted with chloroform
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-eb83bdd704884caf96a92bcef2f7cdc9
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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