Ethanol → N-benzyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 2301496Notes

Reaction equation

HRID 2301496 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:13]=1C(=O)C)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Si](C)(C)C.C([OH:32])C>S(=O)(=O)(O)O>[CH2:1]([NH:8][S:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:13]=1[OH:32])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 17927784N-Benzyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide

Product 1

HCID 18373553N-benzyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of N-benzyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide (225 mg, 0.59 mmol), 0.1 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 (Na2SO4) and concentrated to give the desired product (189 mg, 94%). 1H NMR (DMSO-d6): δ 7.92 (d, 1H), 7.18 (m, 5H), 6.93 (d, 1H), 4.15 (s, 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 (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d61516547ffb4206855a2c12348f762c
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

Loading…