4-(Difluoromethoxy)benzenesulfonyl chloride → 4-Difluoromethoxy-N-[4-methoxy-3-(4-methyl-piperazin-1-yl)-phenyl]-benzenesulfonamide

HRID 1710604Notes

Reaction equation

HRID 1710604 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1>N1C=CC=CC=1>[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[C:18]([N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)[CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 27782234-(Difluoromethoxy)benzenesulfonyl chlorideHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 426028344-Difluoromethoxy-N-[4-methoxy-3-(4-methyl-piperazin-1-yl)-phenyl]-benzenesulfonamideYield 81.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.18 mL of 4-difluoromethoxybenzene sulfonyl chloride (1.13 mmol) were added to a solution of 0.25 g of (1.13 mmol) 4-methoxy-3-(4-methyl-piperazin-1-yl)-phenylamine in 10 mL of pyridine. The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated at reduced pressure. After addition of toluene and dichloromethane the mixture was again evaporated twice. The thus obtained residue was partitioned between dichloromethane and 5% aqueous ammoniumchloride. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The obtained crude product was further purified via HPLC to yield 0.395 g of the desired title compound.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. additionAfter addition of toluene and dichloromethane the mixture
  3. customwas again evaporated twice
  4. customThe thus obtained residue was partitioned between dichloromethane and 5% aqueous ammoniumchloride
  5. washThe organic phase was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained crude product
  10. customwas further purified via HPLC

Sources & evidence

ORD record
ord-7741a19bab1b4660b445be4d6848dd4f
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

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