Water → N-(6-bromo-2-chloropyridin-3-ylcarbamothioyl)benzamide

HRID 241014Notes

Reaction equation

HRID 241014 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:14][C:15]1[N:20]=[C:19]([Cl:21])[C:18]([NH2:22])=[CH:17][CH:16]=1.O>CC(C)=O>[Br:14][C:15]1[N:20]=[C:19]([Cl:21])[C:18]([NH:22][C:2]([NH:3][C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[S:1])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 20500856-Bromo-2-chloropyridin-3-amine

Product 1

HCID 86647817N-(6-bromo-2-chloropyridin-3-ylcarbamothioyl)benzamideYield 89.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of ammonium thiocyanate (0.4 g, 5.0 mmol) in acetone (5 mL) was slowly added benzoyl chloride (0.6 mL, 5.0 mmol) and the suspension was heated to reflux for ten minutes. A solution of 6-bromo-2-chloro-3-pyridinamine (1.0 g, 4.8 mmol) in acetone (10 mL) was then added and the reaction mixture was refluxed for one hour. After cooling to room temperature the mixture was poured into water and partitioned with ethyl acetate (250 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×, 100 mL). The combined organic layers were washed with brine (2×, 100 mL), dried over sodium sulfate, filtered and concentrated until a suspension formed. The white solid was collected by filtration to give N-(6-bromo-2-chloropyridin-3-ylcarbamothioyl)benzamide (1.6 g, 89%). 1H NMR (400 MHz, d6-DMSO): 12.62 (br s, 1H), 12.00 (br s, 1H), 8.37 (d, 1H), 8.00 (2d, 2H), 7.79 (d, 1H), 7.69 (t, 1H), 7.57 (t, 2H). MS (EI) for C13H9BrClN3OS: 370 (MH+).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for ten minutes
  3. temperaturethe reaction mixture was refluxed for one hour
  4. custompartitioned with ethyl acetate (250 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with ethyl acetate (2×, 100 mL)
  7. washThe combined organic layers were washed with brine (2×, 100 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated until a suspension
  11. customformed
  12. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-4e71c3a1c07e4981b490d053c8a95ef5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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