HCID 9966974, compound → HCID 22996556, compound

HRID 1167244Notes

Reaction equation

HRID 1167244 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[C:4]([CH3:17])[CH:3]=1.[C:18]([Cu])#[N:19]>CN(C=O)C.O.C(OCC)(=O)C>[C:18]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[C:4]([CH3:17])[CH:3]=1)#[N:19]

Participants

6

Reactant 2

HCID 9966974HCID 9966974, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22996556HCID 22996556, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 4-bromo-2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide (450 mg, 1.42 mmol) in dry DMF (14 mL) under argon was added CuCN (178 mg, 1.99 mmol). The resulting mixture was heated to 115° C. and stirred for 4 h. The reaction was cooled and diluted with water and ethyl acetate. The layers were separated, and the organics were washed once with water. The organics were then dried, concentrated, and purified by flash chromatography (35% ethyl acetate/hexanes) to provide 4-cyano-2-methyl-5-nitro-(N,N-dimethyl)benzenesulfonamide (249 mg, 65%) as pale yellow crystals. IR (thin film): 2240 cm−1. 1H NMR (400 MHz, CDCl3): δ2.78 (s, 3), 2.94 (s, 6), 7.87 (s, 1), 8.74 (s, 1).

Workup

  1. temperatureThe reaction was cooled
  2. customThe layers were separated
  3. washthe organics were washed once with water
  4. customThe organics were then dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography (35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5735738f169a4b539c7eb90475bc679b
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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