Carbon Disulfide → (2-{[(5-Methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamodithioic acid

HRID 372268

Reaction equation

HRID 372268 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[C:12](=[S:14])=[S:13]>C(O)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12](=[S:13])[SH:14]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Product 1

HCID 15566013(2-{[(5-Methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamodithioic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-((5-methyl-4-imidazolyl)methylthio)ethylamine (10.2 g) in ethanol (75 ml) was added slowly, with stirring, to carbon disulphide (200 ml). The mixture was set aside overnight at room temperature and the solid formed was collected and recrystallised from aqueous isopropyl alcohol to afford N-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]dithiocarbamic acid (9.8 g), m.p. 127°-129°. This was treated with dicyclohexylcarbodiimide in dry pyridine at -10°, and the mixture was filtered. The filtrate was evaporated to dryness and the residue was treated sith ethanolic hydrogen chloride to give 5-methyl-4-(2-isothiocyanatoethylthiomethyl)imidazole hydrochloride.

Workup

  1. customthe solid formed
  2. customwas collected
  3. customrecrystallised from aqueous isopropyl alcohol

Sources & evidence

ORD record
ord-d1d9af87a0e9408d9417ba1c529e7d42
Source dataset
uspto-grants-1978_05
Patent number
US04090026

Linked notes

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