Ethanol → n-Allyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 2301520Notes

Reaction equation

HRID 2301520 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1C(=O)C)(=[O:7])=[O:6])[CH:2]=[CH2:3].Cl[Si](C)(C)C.C([OH:28])C>S(=O)(=O)(O)O>[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[OH:28])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 17927826N-allyl-2-acetyl-6-chloro-3-nitro-benzenesulfonamide

Product 1

HCID 18373503n-Allyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of N-allyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide (30 mg, 009 mmol), 0.mL of chlorotrimethylsilane and 2 drops of fuming sulfuric acid in ethanol was heated to reflux for 20 hours. The solvent was evaporated. The residue was diluted with ethyl acetate and washed with water. The organic layer was then dried (Na,SO4) and concentrated to give the desired product (26 mg, 100%). 1H NMR (MeOD-d4): δ 8.01(d, 1H), 7.20 (d, 1H), 5.70 (m, 1H), 5.16 (m, 1H), 5.05 (m, 1H), 3.62 (m, 2H).

Workup

  1. temperatureto reflux for 20 hours
  2. customThe solvent was evaporated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was then dried (Na,SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb429bc0306647629182470d19fcfa2d
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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