Ethylamine → HCID 178464595, compound

HRID 1711170Notes

Reaction equation

HRID 1711170 reaction equation
[CH3:1][S:2][C:3](SC)=[N:4][C:5]#[N:6].[CH2:9]([NH2:11])[CH3:10]>CO>[CH2:9]([NH:11][C:3](=[N:4][C:5]#[N:6])[S:2][CH3:1])[CH3:10]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 66289Dimethyl N-cyanodithioiminocarbonate

Product 1

HCID 178464595HCID 178464595, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl cyanodithioiminocarbonate (2.85 g, 17.6 mmol) in methanol (20 mL) was added ethylamine (2M soln, 9.7 mL, 19.4 mmol). The solution was allowed to stir at reflux overnight. The solution was cooled to room temperature and the desired product crystallized out of solution over 2 hours. The crystals were collected on a buchner funnel, washed with cold methanol several times, and dried in vacuo to give 1-ethyl-2-methyl-3-cyanoisothiourea as a white solid (1.08 g, 43%). 1H NMR (CDCl3) δ 1.22 (t, 3H, J=6 Hz), 2.61 (s, 3H), 3.35 (s, 1H), 3.46 (q, 2H, J=6 Hz).

Workup

  1. temperatureat reflux overnight
  2. customthe desired product crystallized out of solution over 2 hours
  3. customThe crystals were collected on a buchner funnel
  4. washwashed with cold methanol several times
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8694c27d8c8647b3a41282a4a24a66ff
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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