Benzoyl chloride → HCID 10054324, compound

HRID 36194Notes

Reaction equation

HRID 36194 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31](=[O:34])(=[O:33])[NH2:32])=[CH:21][CH:20]=2)[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>N1C=CC=CC=1>[C:35]([NH:32][S:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:6]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][N:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])[C:7]2=[O:17])=[CH:20][CH:21]=1)(=[O:33])=[O:34])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 100288154''-[3-Butyl-1-(2-chloro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid amide

Product 1

HCID 10054324HCID 10054324, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 41.4 mg (0.0834 mmole) of 5-n-butyl-2-(2-chlorophenyl)-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step B) in 1 ml of dry pyridine stirred at room temperature under argon was added 97 μl (117 mg, 0.836 mmole) of benzoyl chloride. The resulting solution was stirred at room temperature for 12 hours and then treated with saturated NaH2PO4 solution. The mixture was extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was flash chromatographed twice on silica gel (elution with 6-7% MeOH in CH2Cl2 containing 0.2-0.4% concd. NH4OH) to give 30 mg (60%) of the title compound as a white solid; satisfactory purity by TLC in 94:6:0.2 CH2Cl2 --MeOH-concd. NH4OH; mass spectrum (FAB) m/e 601 (M+1)+.

Workup

  1. extractionThe mixture was extracted 3× with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed twice on silica gel (elution with 6-7% MeOH in CH2Cl2 containing 0.2-0.4% concd. NH4OH)

Sources & evidence

ORD record
ord-cd9752018f2d40d0954573c0f4d0e46f
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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