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

HRID 263236Notes

Reaction equation

HRID 263236 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-methylisothiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-[2-aminoethylthiomethyl]-3methoxypyridine (2.1g 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-b1fc137b4b924cb6af38d3a868da332f
Source dataset
uspto-grants-1979_05
Patent number
US04156727

Reaction notes

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