Benzoyl chloride → N-(pyrazin-2-ylcarbamothioyl)benzamide

HRID 1715228Notes

Reaction equation

HRID 1715228 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.[NH2:14][C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1>CC(C)=O>[N:16]1[CH:17]=[CH:18][N:19]=[CH:20][C:15]=1[NH:14][C:2]([NH:3][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:1]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 78747Aminopyrazine

Product 1

HCID 14460677N-(pyrazin-2-ylcarbamothioyl)benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ammonium thiocyanate (17.8 g, 0.234 mol) in dry acetone (200 ml) at 0° C. under nitrogen is added benzoyl chloride (30 g, 0.213 mol) slowly over a period of 15 min. The reaction mixture is stirred at room temperature for 30min and filtered. To the filtrate is added 2-amino pyrazine (16.2 g, 0.17 mol) dropwise and stirred for 3 h at room temperature. The solvent is removed under vacuum and the residue is diluted with water. The solid precipitated is filtered and dried to afford N-[(pyrazin-2-ylamino)carbonothioyl]benzamide as a solid (33 g; 76%). TLC—Chloroform/methanol (9/1): Rf−0.5.

Workup

  1. filtrationfiltered
  2. stirringstirred for 3 h at room temperature
  3. customThe solvent is removed under vacuum
  4. additionthe residue is diluted with water
  5. customThe solid precipitated
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-727f384ed81049c39d2257d227129f1a
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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