Hydrochloric Acid → N-allyl-2-acetyl-6-chloro-3-nitro-benzenesulfonamide

HRID 2301519Notes

Reaction equation

HRID 2301519 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].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[CH:25]=[CH2:26].Cl>CN(C)C=O>[CH2:26]([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])[CH:25]=[CH2:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 183734452-Acetyl-6-chloro-3-nitrobenzenesulfonamide

Product 1

HCID 17927826N-allyl-2-acetyl-6-chloro-3-nitro-benzenesulfonamideYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-acetyl-6chloro-3-nitrobenzenesulfonamide (150 mg, 0.51 mmol), potassium carbonate (84 mg, 0.61 mmol) and allyl bromide (0.18mL, 2.mmol) in 3 mL of N, N-dimethylformamide was heated to 60° C. for 4 days. The mixture was acidified with 1 N aq. HCl, then extracted with ethyl acetate. The solvent was concentrated to give the crude material. Colurnt chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v), gave the desired product (40 mg, 12%). EI-MS (m/z) 333.3, 335.2 (M−).

Workup

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

Sources & evidence

ORD record
ord-910c73170eb044ccb87eb714fd7034c6
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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