Ethyl isothiocyanatoformate → Ethyl (6-bromo-pyridin-2-ylamino)carbonothioylcarbamate

HRID 925495Notes

Reaction equation

HRID 925495 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[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:4]1[N:3]=[C:2]([NH:1][C:15]([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[S:16])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 57361094Ethyl (6-bromo-pyridin-2-ylamino)carbonothioylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-amino-6-bromopyridine (1) (253.8 g, 1.467 mol) in DCM (2.5 L) cooled to 5° C. was added ethoxycarbonyl isothiocyanate (173.0 mL, 1.467 mol) dropwise over 15 min. The reaction mixture was then allowed to warm to room temp. (20° C.) and stirred for 16 h. Evaporation in vacuo gave a solid which was collected by filtration, thoroughly washed with petrol (3×600 mL) and air-dried to afford (2). The thiourea was used as such in the next step without any purification.

Workup

  1. customEvaporation in vacuo
  2. customgave a solid which
  3. filtrationwas collected by filtration
  4. washthoroughly washed with petrol (3×600 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-24027aa5f0fa44339fa78a8736ffb427
Source dataset
uspto-grants-2016_03
Patent number
US09284311B2

Reaction notes

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