Aminopyrazine → Ethyl [(pyrazin-2-yl)carbamothioyl]carbamate

HRID 593033Notes

Reaction equation

HRID 593033 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].[C:8]([N:13]=[C:14]=[S:15])(=[O:12])[O:9][CH2:10][CH3:11]>O1CCOCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:14]([NH:13][C:8](=[O:12])[O:9][CH2:10][CH3:11])=[S:15]

Participants

4

Reactant 2

HCID 78747AminopyrazineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 15619487Ethyl [(pyrazin-2-yl)carbamothioyl]carbamateYield 77.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with pyrazin-2-amine (7.6 g, 80.0 mmol, 1.0 eq.), O-ethyl carbonisothiocyanatidate (12.5 g, 95.4 mmol, 1.2 eq.), and dioxane (150 mL). The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, it was concentrated to a volume of around 20 mL under reduced pressure and the resulting suspension was filtered. The solid was collected and washed with ethyl acetate (3×20 mL) to afford 270a (14.0 g, 77%) as a white solid. MS-ESI: [M+H]+ 227.3

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationit was concentrated to a volume of around 20 mL under reduced pressure
  3. filtrationthe resulting suspension was filtered
  4. customThe solid was collected
  5. washwashed with ethyl acetate (3×20 mL)

Sources & evidence

ORD record
ord-4fd3789ea5ed46c0be662260c9ed29c5
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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