Hydrochloric Acid → N-Methyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide

HRID 2301503Notes

Reaction equation

HRID 2301503 reaction equation
[C:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:5]=1[S:14]([NH2:17])(=[O:16])=[O:15])(=[O:3])[CH3:2].[H-].[Na+].I[CH3:21].Cl>CN(C)C=O>[CH3:21][NH:17][S:14]([C:5]1[C:6]([Cl:13])=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[C:1](=[O:3])[CH3:2])(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 183734452-Acetyl-6-chloro-3-nitrobenzenesulfonamide

Product 1

HCID 18373542N-Methyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-acetyl-6-chloro-3-nitrobenzenesulfonamide (300 mg, 1.02 mmol) and sodium hydride (53 mg, 1.32 mmol) in 10 mL of N,N-dimethylformamide, iodomethane (70 μL, 1.12 mmol) was added. The mixture was stirred at room temperature for 66 hours. The mixture was acidified with 1 N aq. HCl, then extracted with ethyl acetate. The solvent was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v), gave the desired product (185 mg, 59%). EI-MS (m/z) 307.3, 309.3 (M−).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. concentrationThe solvent was concentrated
  4. customto give the crude material
  5. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v)

Sources & evidence

ORD record
ord-fa600434fc4543278390cd97db5f2c20
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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