Hydrochloric Acid → 3-cyano-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 1045199Notes

Reaction equation

HRID 1045199 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[H-].[Na+].[C:11]([C:13]1[CH:14]=[C:15]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:16]=[CH:17][C:18]=1F)#[N:12].Cl>O1CCCC1.O>[C:11]([C:13]1[CH:14]=[C:15]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:16]=[CH:17][C:18]=1[O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)#[N:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 251398973-Cyano-4-fluorobenzene-1-sulfonamide

Product 1

HCID 671264133-cyano-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To (tetrahydro-2H-pyran-4-yl)methanol (0.206 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.284 g) and the reaction stirred at room temperature for 20 minutes. The reaction was cooled to 0° C. and 3-cyano-4-fluorobenzenesulfonamide (0.355 g) in tetrahydrofuran (2 mL) was added dropwise and the reaction was allowed to warm to room temperature. After 3 hours, the reaction was poured into water, made acidic (pH=1) with 1N HCl and extracted with dichloromethane (2×75 mL). The organics were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. waitAfter 3 hours
  4. extractionextracted with dichloromethane (2×75 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-49ab25b6ab8a4d98ba80bd02866bc14b
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

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