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

HRID 1054338Notes

Reaction equation

HRID 1054338 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]>ClCCl>[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

Procedure

To a solution of 2-amino-6-bromopyridine (25 g, 144.5 mmol) in dichloromethane (25 mL) cooled to 5° C. was added ethoxycarbonyl isothiocyanate (17.1 mL, 144.5 mmol) dropwise over 15 min. The reaction mixture was then allowed to warm to room temperature at which it was stirred for 16 h. Evaporation in vacuo gave a yellow solid, which was collected by filtration and thoroughly washed with cyclohexane. No further purification was required. Yield: 41.5 g, 94%; LCMS method: 1, RT: 5.66 min, MI: 304-306 [M+1].

Workup

  1. customEvaporation in vacuo
  2. customgave a yellow solid, which
  3. filtrationwas collected by filtration
  4. washthoroughly washed with cyclohexane
  5. customNo further purification

Sources & evidence

ORD record
ord-76cc6d557adf4d5ba20fa52adf0b01f3
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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