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

HRID 1971525Notes

Reaction equation

HRID 1971525 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-c0521994d01647be82575408e41f4e4b
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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