Benzoyl isothiocyanate → 2-Bromo-6-benzoylthioureidopyridine

HRID 929661Notes

Reaction equation

HRID 929661 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]([N:17]=[C:18]=[S:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)=O>[Br:8][C:4]1[N:3]=[C:2]([NH:1][C:18]([NH:17][C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[S:19])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 206355402-Bromo-6-benzoylthioureidopyridineYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

2.604 g (14.75 mmol) 2-amino-6-bromopyridine was dissolved in 20 mL acetone, and 2.02 mL (14.75 mmol) undiluted benzoyl isothiocyanate was then added dropwise. The solution turned a brown color. The reaction mixture was then heated for 2 hr at 65° C. (oil bath temperature) with stirring. The light yellow solid which formed was filtered under vacuum and washed with pentane. The solvent of the mother liquor was also removed under vacuum. The resulting solids from the crystallizate (1.338 g) and from the mother liquor (3.595 g) were identical according to thin-layer chromatography (silica gel, eluents: dichloromethane/methanol (9:1)). A total of 4.933 g (14.67 mmol, 99.5%) N-{[(6-bromopyridin-2-yl)amino]carbonothioyl}benzamide was isolated.

Workup

  1. customThe light yellow solid which formed
  2. filtrationwas filtered under vacuum
  3. washwashed with pentane
  4. customThe solvent of the mother liquor was also removed under vacuum

Sources & evidence

ORD record
ord-5b077f559e7141df8eb996e5969302bd
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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