Ethyl isothiocyanatoformate → 5-Methoxypyridin-2-amine ethoxycarbonyl thiourea

HRID 250018Notes

Reaction equation

HRID 250018 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH2:10]([O:12][C:13]([N:15]=[C:16]=[S:17])=[O:14])[CH3:11]>O1CCOCC1>[CH2:10]([O:12][C:13]([NH:15][C:16]([NH2:7])=[S:17])=[O:14])[CH3:11].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 113209342-Amino-5-methoxypyridine

Product 1

HCID 866352895-Methoxypyridin-2-amine ethoxycarbonyl thioureaYield 201.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 5-methoxypyridin-2-amine (5 g, 40 mmol) in dioxane (40 mL) was added ethoxycarbonyl isothiocyanate (5.23 mL, 44.3 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo to afford 5-methoxypyridin-2-amine ethoxycarbonyl thiourea (10.28 g, 40.3 mmol, 100% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.03 (1 H, br. s.), 11.37 (1 H, br. s.), 8.53 (1 H, br. s.), 8.11 (1 H, d, J=2.93 Hz), 7.50 (1 H, dd, J=8.97, 3.11 Hz), 4.22 (2 H, q, J=7.07 Hz), 3.84 (3 H, s), 1.26 (3 H, t, J=7.14 Hz). MS (LC/MS) R.T.=2.40; [M+H]+=256.1.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-222b19def4df4654a04767a99799547a
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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