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

HRID 537730Notes

Reaction equation

HRID 537730 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]>C(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[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 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-amino-5-bromopyridine (1) (200.0 g, 1.156 mol) in DCM (2.0 L) cooled to 5° C. was added ethoxycarbonyl isothiocyanate (134.9 mL, 1.156 mol) dropwise over 15 min. The reaction mixture was then allowed to warm to room temperature (20° C.) and stirred for 16 h. Evaporation in vacuo gave a yellow solid which was collected by filtration, thoroughly washed with petrol (3×500 mL) and air-dried to afford the title compound (351.5 g, quantitative). No further purification was required.

Workup

  1. customEvaporation in vacuo
  2. customgave a yellow solid which
  3. filtrationwas collected by filtration
  4. washthoroughly washed with petrol (3×500 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-e55a7f9ade284d26adfb5ef3206d0fcf
Source dataset
uspto-grants-2014_10
Patent number
US08865699B2

Reaction notes

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