P-Toluenesulfonylhydrazide → HCID 18428684, compound

HRID 1279631Notes

Reaction equation

HRID 1279631 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7](/[CH:20]=[CH:21]/[S:22]([NH2:25])(=[O:24])=[O:23])[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[CH3:3].S(NN)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:20][CH2:21][S:22]([NH2:25])(=[O:23])=[O:24])[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[CH3:3]

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 18428734HCID 18428734, compound

Product 1

HCID 18428684HCID 18428684, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The vinylsulfonamide from example 67 (1.26 g, 3.33 mmol) was heated together with tosyl hydrazine (6.20 g, 33.3 mmol) in toluene at reflux for 5 h. After cooling to rt the solvent was evaporated and the residue partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, washed with water (20 mL), brine (20 mL) and then dried (MgSO4) and evaporated. The residue was purified by flash chromatography [SiO2; (EtOAc/ MeOH/ 880 NH3; 100:5:0.5)/ pentane; 3:1→1:0] to afford the desired product as a cream powder (1.055 g, 83%); Free base: δH(CD3OD, 400 MHz) 2.27 (6 H, s), 2.47 (3 H, s), 3.09-3.13 (2 H, m), 3.30-3.36 (2 H, m), 3.50 (2 H, m), 6.83 (1 H, d), 6.87 (2 H, d), 7.19 (1 H, d), 7.27 (2 H, d), 7.35 (1 H, s); MS m/z (TS+) 381 (MH+).

Workup

  1. temperatureat reflux for 5 h
  2. customwas evaporated
  3. customthe residue partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL)
  4. customThe organic layer was separated
  5. washwashed with water (20 mL), brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash chromatography [SiO2; (EtOAc/ MeOH/ 880 NH3; 100:5:0.5)/ pentane; 3:1→1:0]

Sources & evidence

ORD record
ord-ace9b134c9704260af4bd87dfc9ecdc4
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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