Benzoyl isothiocyanate → HCID 59286693, compound

HRID 1876018Notes

Reaction equation

HRID 1876018 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10]([N:18]=[C:19]=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O>[Cl:1][C:2]1[C:3]([NH:9][C:19]([NH:18][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[S:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 778863,5-Dichloro-3-pyridylamine

Product 1

HCID 59286693HCID 59286693, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3,5-dichloropyridin-2-amine (3.87 g, 23.73 mmol) in acetone (20 mL) was added benzoyl isothiocyanate (3.2 mL, 23.73 mmol). The mixture was stirred at ambient temperature for 1 h, and the resultant precipitate was collected by filtration (3.89 g). The filtrate was returned to the reaction flask and heated to reflux 1 h. At this time, the reaction had gone dry. The solids were suspended in acetone and collected by filtration to give 2.24 g. of N-(3,5-dichloropyridin-2-ylcarbamothioyl)benzamide (5.93 g, 18.18 mmol, 77% yield). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 12.78 (br. s., 1H) 9.25 (br. s., 1H) 8.46 (br. s., 1H) 7.94 (d, J=7.63 Hz, 2H) 7.88 (d, J=2.44 Hz, 1H) 7.69 (t, J=7.48 Hz, 1H) 7.58 (t, J=7.78 Hz, 2H).

Workup

  1. filtrationthe resultant precipitate was collected by filtration (3.89 g)
  2. temperatureheated
  3. temperatureto reflux 1 h
  4. customAt this time, the reaction had gone dry
  5. filtrationcollected by filtration
  6. customto give 2.24 g

Sources & evidence

ORD record
ord-67edb7ae732c4ff8bae3028d2b570b15
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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