Ethyl isothiocyanatoformate → Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

HRID 451458

Reaction equation

HRID 451458 reaction equation
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>O1CCOCC1>[Br:1][C:2]1[C:3]([NH:8][C:15]([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[S:16])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformate2×HCID 8177002-Amino-3-bromopyridine

Product 1

HCID 59199107Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Bromopyridin-2-amine (30 g, 168 mmol) and ethoxycarbonyl isothiocyanate (24.8 g, 21.3 mL, 185 mmol) were dissolved in dioxane (300 mL) and stirred at room temperature. After 4 hours further ethoxycarbonyl isothiocyanate (1 mL, 8.4 mmol) was added. After 1 hour the solvent was evaporated and the residue dried in high vacuum for 12 hours. The title compound was obtained as a light yellow solid (51.2 g, 100%) and was used crude for the next step.

Workup

  1. customAfter 1 hour the solvent was evaporated
  2. customthe residue dried in high vacuum for 12 hours

Sources & evidence

ORD record
ord-a9bcd574b9cf4198bd995cafa9a169f3
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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