P-Toluenesulfonylhydrazide → HCID 10741632, compound

HRID 725024Notes

Reaction equation

HRID 725024 reaction equation
[C:1]1([S:7]([CH:10]=[CH:11][C:12]2[CH:13]=[C:14]([CH:22]=[C:23]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:24]=2)[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(NN)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:22]=[C:23]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:24]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 53958779HCID 53958779, compound

Product 1

HCID 10741632HCID 10741632, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3-(2-phenylsulphonylethenyl)-5-(3-pyridylmethyl)cinnamate (preparation 20; 0.485 g) and 4-methylphenylsulphonyl hydrazine (2.08 g) in toluene (25 ml) was heated under reflux for 3 hours and then evaporated under vacuum. The residue was chromatographed on silica gel using an ethyl acetate in hexane elution gradient (50 to 100% ethyl acetate) initially followed by an ethyl acetate:diethylamine (95:5) mixture as eluent. The product fractions were combined and evaporated under vacuum to give the title compound as a gum (0.384 g); Rf 0.50 (SS 4); δ (CDCl3): 1.23(3H,t), 2.57(2H,t), 2.86(2H,t), 2.99(2H,m), 3.33(2H,m), 3.91(2H,s), 4.13(2H,q), 6.82(1H,s), 6.87(1H,s), 6.91(1H,s), 7.22-7.25(1H,m), 7.43-7.47(1H,m), 7.57-7.72(3H,m), 7.94-7.98(2H,m), 8.48-8.51(2H,m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated under vacuum
  4. customThe residue was chromatographed on silica gel using
  5. washan ethyl acetate in hexane elution gradient (50 to 100% ethyl acetate)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-71187d15fada4c8e98d4e8ae716d671a
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

Loading…