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

HRID 2058208Notes

Reaction equation

HRID 2058208 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:15]([N:17]=[C:18](SC)[S:19][CH3:20])#[N:16]>C(O)C>[C:15]([NH:17][C:18](=[N:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][N:7]=1)[S:19][CH3:20])#[N:16]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 204022362-(2-Aminoethylthiomethyl)-3-ethoxypyridine

Product 1

HCID 20474235N-cyano-N'-[2-((3-ethoxy-2-pyridyl)methylthio)ethyl]-S-methylisothioureaYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(2-Aminoethylthiomethyl)-3-ethoxypyridine (1.0 g) in ethanol (10 cc) was added over 45 minutes to a stirred solution of dimethyl N-cyanodithioimidocarbonate (0.690 g) in ethanol (5 cc) at room temperature. The mixture was allowed to stand overnight at room temperature, nitrogen was bubbled through the solution for one hour, and the mixture was allowed to crystallise to give N-cyano-N'-[2-((3-ethoxy-2-pyridyl)methylthio)ethyl]-S-methylisothiourea (1.4 g) m.p. 98°-99°.

Workup

  1. customnitrogen was bubbled through the solution for one hour
  2. customto crystallise

Sources & evidence

ORD record
ord-1f4b9f7056ac4efaa8f874c498d5ac88
Source dataset
uspto-grants-1980_07
Patent number
US04215126

Reaction notes

Loading…