Benzoyl isothiocyanate → HCID 86098775, compound

HRID 929665Notes

Reaction equation

HRID 929665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH: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:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][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:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 86098775HCID 86098775, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.500 g (14.01 mmol) 4-bromopyridine-2-amine was dissolved in 20 mL acetone, and 1.92 mL (14.01 mmol) undiluted benzoyl isothiocyanate was added dropwise. The solution turned an orange color. The reaction mixture was then heated for 1 hr under reflux with stirring. Half of the added quantity of acetone was removed under vacuum, and the precipitated solid was filtered under vacuum and washed with diethyl ether. After drying of the crystallizate, 3.500 g (10.410 mmol, 74%) pure N-{[(4-bromopyridin-2-yl)amino]carbonothioyl}benzamide was obtained which was directly used for further reaction.

Workup

  1. temperatureThe reaction mixture was then heated for 1 hr
  2. temperatureunder reflux
  3. customHalf of the added quantity of acetone was removed under vacuum
  4. filtrationthe precipitated solid was filtered under vacuum
  5. washwashed with diethyl ether
  6. customAfter drying of the crystallizate

Sources & evidence

ORD record
ord-3f52269ef9ac4699992cc361d49f8759
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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