2-Amino-5-bromopyridine → Ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamate

HRID 241016Notes

Reaction equation

HRID 241016 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>O1CCOCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]([NH:14][C:12](=[O:13])[O:11][CH2:9][CH3:10])=[S:16])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 59286274Ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamateYield 70.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-bromopyridine (5.0 g, 29 mmol) in dioxane (60 mL) was added ethoxycarbonylisothiocyanate (3.4 mL, 29 mmol) in a dropwise manner and the mixture was allowed to stir for 18 h at room temperature. The mixture was then concentrated and the residue triturated with 10% ethyl acetate in hexanes. The solid was collected by filtration and dried to afford ethyl {[(5-bromopyridin-2-yl)amino]carbonothioyl}carbamate (6.2 g, 69%) as a colorless solid. MS (EI) for C9H10BrN3O2S: 305 (MH+).

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue triturated with 10% ethyl acetate in hexanes
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f7ae42fca88149fdbd1c316f268653ce
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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