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

HRID 20584

Reaction equation

HRID 20584 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10422Azetidine

Product 1

HCID 59346928Azetidine, 1-[(4-fluorophenyl)sulfonyl]-Yield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Azetidine (0.25 g, 4.35 mmol) was added to a solution of sodium hexamethyldisilylazide (0.85 g, 4.6 mmol) in THF (10 mL) at 0° C. and reaction mixture stirred for 10 minutes. 4-fluorobenzenesulfonyl chloride (0.85 g, 4.35 mmol) was subsequently added and the reaction mixture was allowed to warm up to ambient temperature overnight. The reaction mixture was concentrated in vacuo and the residue taken up in ethyl acetate and water. The organic layer was separated and then dried (MgSO4), filtered and evaporated to give a waxy, yellow solid (75 mg).

Workup

  1. customreaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c32ba789be974ba99759bf5cf8743db1
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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