Hydrochloric Acid → 3-(1-Hydroxycyclobutyl)benzenesulfonamide

HRID 2303579Notes

Reaction equation

HRID 2303579 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:13]2([OH:17])[CH2:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C([O-])(=O)C.[Na+].[NH:23]([S:25](O)(=[O:27])=[O:26])O.Cl>CCCCCC.O1CCCC1>[OH:17][C:13]1([C:9]2[CH:8]=[C:7]([S:25]([NH2:23])(=[O:27])=[O:26])[CH:12]=[CH:11][CH:10]=2)[CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 170246Hydroxysulfamic acidHCID 517045Sodium AcetateHCID 184615711-(3-Bromophenyl)-cyclobutanolHCID 178418339Butyllithium

Product 1

HCID 184617223-(1-Hydroxycyclobutyl)benzenesulfonamideYield 4.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.6M solution of n-butyllithium (8 ml, 12.8 mmol) in hexane was added to a solution of 1-(3-bromo-phenyl)cyclobutanol (1.44 grams, 6.4 mmol) in tetrahydrofuran at −78° C. After 30 minutes, at the reaction was allowed to warm to 0° C. Sulfur dioxide was bubbled into the reaction mixture and stirred for an additional 30 minutes. The tetrahydrofuran was evaporated and an aqueous solution of sodium acetate (4.1 grams, 50 mmol) and of hydroxylamine-sulfonic acid (1.85 grams, 16 mmol) was added. After stirring at room temperature for 2 hours, the reaction was acidified with 2N hydrochloric acid then extracted with ethyl acetate. The ethyl acetate was dried over sodium sulfate and evaporated. The residue was purified on silica gel with dichloromethane/ether to give 70 mg of the titled compound.

Workup

  1. customSulfur dioxide was bubbled into the reaction mixture
  2. customThe tetrahydrofuran was evaporated
  3. stirringAfter stirring at room temperature for 2 hours
  4. extractionthen extracted with ethyl acetate
  5. dry with materialThe ethyl acetate was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified on silica gel with dichloromethane/ether

Sources & evidence

ORD record
ord-d4a3509bef3b495aa0082a3b932c6cbe
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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