4-Fluorobenzenesulfonyl chloride → Azetidine, 1-[(4-fluorophenyl)sulfonyl]-

HRID 1964587Notes

Reaction equation

HRID 1964587 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]2[CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 12308726Azetidine hydrochloride

Product 1

HCID 59346928Azetidine, 1-[(4-fluorophenyl)sulfonyl]-Yield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Commercially available 4-fluorophenylsulfonylchloride (225 mg, 1.15 mmol) was suspended in water (8 mL), and azetidine hydrochloride (90.0 mg, 0.96 mmol) and potassium carbonate (293 mg, 2.12 mmol) were added, followed by stirring at room temperature for 16 hours. To the reaction solution, water (15 mL) was added, followed by extraction twice with diethyl ether (15 mL), and washing was carried out with saturated brine (15 mL), followed by drying over sodium sulfate. The solvent was distilled off under reduced pressure, followed by vacuum drying, to afford the desired compound (170 mg, yield 82%) as a white solid.

Workup

  1. extractionfollowed by extraction twice with diethyl ether (15 mL)
  2. washwashing
  3. dry with materialby drying over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customdrying

Sources & evidence

ORD record
ord-473b266cfcb2464a953daa10f1d166f1
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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