Azetidine → 1-[(5-Bromo-2-thienyl)sulfonyl]azetidine

HRID 387335Notes

Reaction equation

HRID 387335 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[Br:5][C:6]1[S:10][C:9]([S:11](Cl)(=[O:13])=[O:12])=[CH:8][CH:7]=1>C(Cl)Cl>[Br:5][C:6]1[S:10][C:9]([S:11]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:13])=[O:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 593327961-[(5-Bromo-2-thienyl)sulfonyl]azetidineYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Azetidine (0.258 mL, 3.82 mmol) was added to a solution of 5-bromo-2-thiophenesulfonyl chloride (500 mg, 1.912 mmol) in DCM (4.8 mL) in a 4 dram vial. The reaction was stirred at room temperature for 5 min. The reaction mixture was concentrated under a stream of nitrogen at 50° C. and dried under high vacuum. The residue was taken up in EtOAc (10 mL) and extracted with saturated NaHCO3 (2×2 mL). The organic layer was dried (Na2SO4), concentrated under a stream of nitrogen at 50° C., and dried under high vacuum, giving 501 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under a stream of nitrogen at 50° C.
  2. customdried under high vacuum
  3. extractionextracted with saturated NaHCO3 (2×2 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under a stream of nitrogen at 50° C.
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-de23c1cf1ea54975b155d34496d27c43
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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