Benzoyl chloride → HCID 178523937, compound

HRID 1715233Notes

Reaction equation

HRID 1715233 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:19]=[CH:18][NH:17][N:16]=1>CC(C)=O>[NH:17]1[CH:18]=[CH:19][C:15]([NH:14][C:2]([NH:3][C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[S:1])=[N:16]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 178418806HCID 178418806, compound

Product 1

HCID 178523937HCID 178523937, compound

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 benzoylchloride (30 g, 0.213 mol) over a period of 15 min. The reaction mixture is stirred at rt for 30 min and filtered. To the filtrate is added 3-aminopyrazole (14.1 g, 0.17 mol) dropwise and stirred 3 h at room temperature. The solvents are removed under vacuum and the residue is purified by flash chromatography using chloroform/methanol (9/1) as eluent. N-[(1H-pyrazol-3-ylamino)carbonothioyl]benzamide is isolated as a solid (22 g; 52%). M+ (ESI): 246.9. TLC—Chloroform/methanol (9/1): Rf−0.45.

Workup

  1. filtrationfiltered
  2. stirringstirred 3 h at room temperature
  3. customThe solvents are removed under vacuum
  4. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-818c7956117d4775a90b4a164246c69a
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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