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

HRID 588428Notes

Reaction equation

HRID 588428 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>O1CCOCC1>[CH2:9]([O:11][C:12]([NH:14][C:15]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[S:16])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 59286274Ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-bromopyridin-2-amine (14.7 g, 85.0 mmol) and ethoxycarbonyl isothiocyanate (11.1 g, 10.0 ml, 85.0 mmol) in dioxane (300 ml) was stirred for 18 hours at 25° C. under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the solid yellow residue was diluted with ethyl acetate and washed with water and brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated to dryness. 26.2 g (quant.) light yellow solid. Mp.: 159-161° C. MS: m/z=304.0/305.9 (M+H+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe solid yellow residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a28fc3e60fd945a88b73df44313566bc
Source dataset
uspto-grants-2016_01
Patent number
US09227970B2

Reaction notes

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