4-Acetylbenzenesulphonamide → 4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

HRID 10736Notes

Reaction equation

HRID 10736 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=O)[CH:15]([CH3:17])[CH3:16].C[O-].[Li+]>CN(C)C=O>[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27](/[CH:28]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[O:3])[CH:30]=1)[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 219810255-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

Product 1

HCID 117544734-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.18 g, 0.62 mmol) in N,N-dimethylformamide (9 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The reaction was quenched with water. The aqueous solution was washed ethyl acetate, acidified to pH 5, extracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane). The combined dichloromethane and isopropyl alcohol was washed with brine, dried over sodium sulfate and concentrated. The crude product was then stirred in ethanol (50%, v/v, in acetone) to give the title compound as a light yellow solid: m.p.>240° C. 1H NMR (DMSO-d6) δ 8.60 (s, 1H), 8.26 (d, J=8.1 Hz, 2H), 8.06 (d, J=15.3 Hz, 1H), 8.07 (s, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.84 (d, J=15.3 Hz, 1H), 7.50 (s, 1H), 6.84 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 3.61 (d, J=7.3 Hz, 2H), 1.81–1.74 (m, 1H), 0.67 (d, J=16.7 Hz, 6H). MS m/z=471 ([M+H]+, 100%).

Workup

  1. customThe reaction was quenched with water
  2. washThe aqueous solution was washed ethyl acetate
  3. extractionextracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane)
  4. washThe combined dichloromethane and isopropyl alcohol was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. stirringThe crude product was then stirred in ethanol (50%, v/v, in acetone)

Sources & evidence

ORD record
ord-96724e89cdcb4f12bbae30db440eb7ce
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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