Dimethyl N-cyanodithioiminocarbonate → HCID 178512076, compound

HRID 2067320Notes

Reaction equation

HRID 2067320 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([N:14]=[C:15](SC)SC)#[N:13]>O1CCOCC1.ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][C:15]1=[N:14][C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 77801N-Benzylethylenediamine

Product 1

HCID 178512076HCID 178512076, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-benzylethane-1,2-diamine (3.00 g, 19.96 mmol) in anhydrous dioxane (15 mL) was added dimethyl cyanocarbonimidodithioate (3.50 g, 23.96 mmol). The mixture was refluxed for 16 hours, then diluted with dichloromethane (200 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/4) to afford the title compound as a colorless solid in 95% yield (3.88 g): mp 120-122° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.36-7.22 (m, 5H), 6.86 (br s, 1H), 4.38 (s, 2H), 3.58-3.52 (m, 2H), 3.44-3.88 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 164.0, 135.5, 128.8, 128.1, 127.9, 119.4, 48.3, 46.1, 40.2; MS (ES+) m/z 201.2 (M+1).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. washwashed with water (200 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluted with ethyl acetate/hexane (1/4)

Sources & evidence

ORD record
ord-5813b7c8c7c64b9f9e974a5bb08266be
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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