Benzoyl chloride → HCID 10075750, compound

HRID 36191Notes

Reaction equation

HRID 36191 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:30])(=[O:29])[NH2:28])=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1>[C:31]([NH:28][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:6]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][N:8]([CH:10]([CH3:11])[CH3:12])[C:7]2=[O:13])=[CH:16][CH:17]=1)(=[O:29])=[O:30])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 152821035-n-Butyl-2,4-dihydro-2-isopropyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 10075750HCID 10075750, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 52.7 mg (0.123 mmole) of 5-n-butyl-2,4-dihydro-2-isopropyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step I) in 1 ml of dry pyridine stirred at room temperature under argon was added 143 μL (173 mg; 1.23 mmole) of benzoyl chloride. After 12 hours at room temperature, the mixture was treated with saturated NaH2PO4 solution and extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography of the residue on silica gel (elution with 4% MeOH and 0.2% ammonium hydroxide in CH2Cl2) gave 42.3 mg (69%) 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 533 (M+1)+.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d45d26adcbac401bbf1c1636b6da8123
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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