Sulfanilamide → HCID 178514725, compound

HRID 1935519Notes

Reaction equation

HRID 1935519 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3=[CH:17]OC(C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:23]([NH2:33])(=[O:32])([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)=[O:24]>Cl.C(O)C>[O:16]=[C:11]1[C:10](=[CH:17][NH:31][C:28]2[CH:29]=[CH:30][C:25]([S:23]([NH2:33])(=[O:24])=[O:32])=[CH:26][CH:27]=2)[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)[NH:12]1

Participants

5

Reactant 2

HCID 5333SulfanilamideHCID 54563562HCID 54563562, compound

Product 1

HCID 178514725HCID 178514725, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.09 g (0.31 mmol) of 5-phenyl-3-tert-butoxymethylene-1,3-dihydro-indol-2-one, 0.053 g (0.31 mmol) of sulfanilamide, and 2 drops of conc. HCl in 15 mL of ethanol was refluxed for 1 h and cooled to rt. The resulting yellow solid was isolated by filtration, washed with ethanol and dried to give 0.068 g (56%) of the title compound: 1H NMR (DMSO-d6): δ 6.90 (d, J=8.2 Hz, 1H), 7.25 (s, 2H), 7.29 (t, J=7.5 Hz, 1H), 7.34 (dd, J=1.6, 8.2 Hz, 1H), 7.43 (d, J=7.5 Hz, 2H), 7.55 (d, J=8.8 Hz, 2H), 7.64 (d, J=7.5 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 7.99 (d, J=1.6 Hz, 1H), 8.74 (d, J=12.5 Hz, 1H), 10.62 (s, 1H), 10.76 (d, J=12.5 Hz, 1H); APCI−MS m/z 390 (M−H)−.

Workup

  1. customThe resulting yellow solid was isolated by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-468f8dfc9927482a81c7b69f7d9c75cf
Source dataset
uspto-grants-2002_05
Patent number
US06387919B1

Reaction notes

Loading…