Dimethyl N-cyanodithioiminocarbonate → N-cyano-N'-[2-((3-methoxy-2-pyridyl)methylthio)ethyl]S-methylisothiourea

HRID 2295870Notes

Reaction equation

HRID 2295870 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:14]([N:16]=[C:17](SC)[S:18][CH3:19])#[N:15]>C(O)C>[C:14]([NH:16][C:17](=[N:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1)[S:18][CH3:19])#[N:15]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 129515352-{[(3-Methoxypyridin-2-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 20474175N-cyano-N'-[2-((3-methoxy-2-pyridyl)methylthio)ethyl]S-methylisothioureaYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-[2-aminoethylthiomethyl]-3-methoxypyridine (2.1 g) in ethanol (15 ml) was added over one hour to a stirred solution of dimethyl N-cyanodithioimidocarbonate (1.5 g) in ethanol (15 ml). The mixture was allowed to stand overnight and nitrogen was bubbled through for one hour. The crystalline precipitate was recrystallised from ethanol/ether to yield N-cyano-N'-[2-((3-methoxy-2-pyridyl)methylthio)ethyl]-S-methylisothiourea (2.2 g), m.p. 102°-103°.

Workup

  1. customnitrogen was bubbled through for one hour
  2. customThe crystalline precipitate was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-6370c94345494549a7dae574928fd4fa
Source dataset
uspto-grants-1984_01
Patent number
US04426526

Reaction notes

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