Water → HCID 66681891, compound

HRID 909521Notes

Reaction equation

HRID 909521 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].Cl.[NH:14]1[CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:14]2[CH2:17][CH2:16][CH2:15]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 12308726Azetidine hydrochloride

Product 1

HCID 66681891HCID 66681891, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 3,4-difluorophenylsulfonylchloride (117 μL, 0.87 mmol) was dissolved in dichloromethane (5 mL), and azetidine hydrochloride (68 mg, 0.73 mmol) and triethylamine (203 μL, 1.45 mmol) were added, followed by stirring at room temperature for 2 hours. To the reaction solution, water (15 mL) was added, and extraction was carried out twice with dichloromethane (15 mL). Washing was carried out with saturated brine (15 mL), followed by drying over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%) to afford the desired compound (132 mg, yield 78%) as a colorless oil.

Workup

  1. extractionextraction
  2. washWashing
  3. dry with materialby drying over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%)

Sources & evidence

ORD record
ord-dbd50252326b4bb4b85caf8a32eeb049
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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