1,4-Dioxane → N-(3-bromo-6-ethoxycarbonyl-pyridin-2-yl)-N'-ethoxycarbonyl-thiourea

HRID 451450Notes

Reaction equation

HRID 451450 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([NH2:12])[N:6]=1)=[O:4].[CH2:13]([O:15][C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH3:14].O1CCOC[CH2:22]1>>[Br:11][C:8]1[C:7]([NH:12][C:19]([NH:18][C:16]([O:15][CH2:13][CH3:14])=[O:17])=[S:20])=[N:6][C:5]([C:3]([O:2][CH2:1][CH3:22])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 85320Ethyl isothiocyanatoformateHCID 10704661Methyl 6-amino-5-bromopicolinate

Product 1

HCID 86656219N-(3-bromo-6-ethoxycarbonyl-pyridin-2-yl)-N'-ethoxycarbonyl-thiourea

Procedure

To a solution of 6-amino-5-bromo-pyridine-2-carboxylic acid methyl ester (3.3 g, 14.28 mmol) in dry 1,4-dioxane (20 mL) was added ethoxy carbonyl isothiocyanate (1.8 mL, 15.7 mmol) under an argon atmosphere and stirred at room temperature for 16 hours. The solvent was evaporated and the title compound was obtained as yellow solid (4.9 g, 95%).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-78544b7f74ca4cd3aceb775c702132bb
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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