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

HRID 444486Notes

Reaction equation

HRID 444486 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-6fece1b6813248d29cc8ff7c310b0342
Source dataset
uspto-grants-1981_04
Patent number
US04264608

Reaction notes

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