Ethyl isothiocyanatoformate → Ethyl [(4,6-dichloropyridin-2-yl)carbamothioyl]carbamate

HRID 712192Notes

Reaction equation

HRID 712192 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[N:13]=[C:12]([NH2:17])[CH:11]=1>O1CCOCC1>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[N:13]=[C:12]([NH:17][C:7]([NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])=[S:8])[CH:11]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 53166492-Amino-4,6-dichloropyridine

Product 1

HCID 59437527Ethyl [(4,6-dichloropyridin-2-yl)carbamothioyl]carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethoxycarbonyl isothiocyanate (2 g, 16 mmol) was added to a solution of 4,6-dichloropyridin-2-amine (2.2 g, 13 mmol) in 1,4-dioxane (100 mL) and stirred at rt for 18 h. LCMS showed desired product. The reaction mixture was concentrated in vacuo and the residue azeotroped with EtOAc (3×20 mL) to give a cream solid, which was triturated with EtOAc to give the desired product as a white solid (2.9 g, 76%). 1H NMR (DMSO) δ 12.31 (s, 1H), 11.77 (s, 1H), 8.86 (d, J=1.1 Hz, 1H), 7.66 (d, J=1.5 Hz, 1H), 4.25 (q, J=7.1 Hz, 2H), 1.28 (t, J=7.1 Hz, 3H). m/z [M+H]+=293.88

Sources & evidence

ORD record
ord-f2912b31653c457698edb565a33481bb
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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