Ethyl isothiocyanatoformate → ethyl-N-[(3,6-dimethylpyrazin-2-yl)carbamothioyl]carbamate

HRID 1054979Notes

Reaction equation

HRID 1054979 reaction equation
[CH3:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.[CH2:10]([O:12][C:13]([N:15]=[C:16]=[S:17])=[O:14])[CH3:11]>O1CCOCC1>[CH2:10]([O:12][C:13](=[O:14])[NH:15][C:16](=[S:17])[NH:9][C:3]1[C:2]([CH3:1])=[N:7][CH:6]=[C:5]([CH3:8])[N:4]=1)[CH3:11]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 132615003,6-Dimethylpyrazin-2-amine

Product 1

HCID 90017035ethyl-N-[(3,6-dimethylpyrazin-2-yl)carbamothioyl]carbamateYield 96.73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3,6-dimethyl-pyrazin-2-ylamine (5 g, 40.65 mmol) in dioxane (150 ml) was added ethoxycarbonyl isothiocyanate (4.75 ml, 40.65 mmol) at 25° C., and the reaction mixture was stirred for 18 hours at 25° C. Volatiles were removed in vacuo. The resultant residue was dissolved in ethyl acetate, washed with water twice, and brine, dried over anhydrous sodium sulfate, filtered, and evaporated affording ethyl-N-[(3,6-dimethylpyrazin-2-yl)carbamothioyl]carbamate (10 g, 96.73%) as a light yellow solid. MS: m/z=255 (M+H+)

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionThe resultant residue was dissolved in ethyl acetate
  3. washwashed with water twice
  4. dry with materialbrine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-02b48816eb334b449f4ff60955937251
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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