Hydrochloric Acid → 2,4-Dichloro-N-(2-chloro-4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

HRID 1827541Notes

Reaction equation

HRID 1827541 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34]C2CCCCO2)=[CH:30][C:29]=1[Cl:41])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].Cl>C(O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=1[Cl:41])[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:17][CH:18]=1)(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221374052,4-dichloro-N-[2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

Product 1

HCID 100992172,4-Dichloro-N-(2-chloro-4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamideYield 34.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude 2,4-dichloro-N-[2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide (0.096 g, 0.15 mmol) in 4 mL absolute ethanol was added 1 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 24 hr. and was diluted with 10 mL saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride (2×10 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/ethyl acetate) to afford 0.029 g of the title compound. MS 557.3 (M+1)+

Workup

  1. washThe aqueous solution was washed with methylene chloride (2×10 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-754c60f628dd40a0a72ad52eaf66a621
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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