Hydrochloric Acid → HCID 22272573, compound

HRID 230475Notes

Reaction equation

HRID 230475 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].Cl>CN(C=O)C>[F:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 22272573HCID 22272573, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzenesulfonamide (3.14 g, 20 mmol) was dissolved in DMF (100 mL) and NaH (60% in oil, 40 mmol, 1.60 g) was added. The reaction was stirred until the gas evolution ceased. 2,4-Difluoronitrobenzene (18 mmol, 2.9 g, 2 mL) was added and the reaction mixture was stirred over night at 35° C. The reaction mixture was poured into HCl (1M aq, 100 mL) and extracted with toluene (25 mL×5). The organic phase was dried (MgSO4) and concentrated and re-crystallized from EtOH to give a first crop of 3.75 g of a yellow solid. A second crop of 0.20 g was collected from the EtOH remains. Yield 3.95 g, 13.3 mmol (74%).

Workup

  1. stirringthe reaction mixture was stirred over night at 35° C
  2. extractionextracted with toluene (25 mL×5)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customre-crystallized from EtOH

Sources & evidence

ORD record
ord-da9e51cb15e643d29f0e4c8adc057fa0
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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