Benzenesulfonyl chloride → HCID 10349512, compound

HRID 1198671Notes

Reaction equation

HRID 1198671 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:38]1([S:44]([NH:35][S:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:25]2[CH:26]=[CH:27][C:22]([CH2:21][N:6]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][N:8]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:16]([F:19])([F:18])[F:17])[C:7]3=[O:20])=[CH:23][CH:24]=2)(=[O:37])=[O:36])(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 10349512HCID 10349512, compound

Conditions

Temperature
60 °C

Procedure

The title compound was prepared from 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 13, Step C) according to the procedure of Example 14, except that a total of 2.4 equivalents of benzenesulfonyl chloride was used, and the mixture was heated at 60° C. for 4 hours. The crude produce was purified by flash chromotography on silica gel (gradient elution with 0.5-5% MeOH in CH2Cl2). The residue from evaporation of the product fractions was partitioned between CH2Cl2 and 1N HCl. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as a cream-colored, sticky solid, homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 671 (M+1)+.

Workup

  1. customThe crude produce
  2. customwas purified by flash chromotography on silica gel (gradient elution with 0.5-5% MeOH in CH2Cl2)
  3. customThe residue from evaporation of the product fractions
  4. customwas partitioned between CH2Cl2 and 1N HCl
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7248b4d65be49e1bfbf94e7885f2a5a
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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