Potassium Carbonate → HCID 25211587, compound

HRID 516802Notes

Reaction equation

HRID 516802 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][OH:9].[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20].S(Cl)(Cl)(=O)=O>O.CO.C1COCC1>[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[O:21])(=[O:20])[NH:8][OH:9]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 25211587HCID 25211587, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium carbonate (3.53 g, 25.57 mmol) in water (3.6 ml) was added dropwise to a solution of hydroxylamine hydrochloride (1.76 g, 25.57 mmol) in water (2.4 ml) at 0° C. maintaining an internal reaction temperature between 5° C. and 15° C. THF (12 ml) and methanol (3 ml) were added, followed by 2-chlorosulfonyl-benzoic acid methyl ester (3 g, 12.78 mmol) portionwise maintaining a temperature below 15° C. and the reaction mixture was stirred at ambient temperature until complete consumption of the sulfonyl chloride was observed by tlc. The resulting suspension was concentrated to remove any volatiles and the aqueous suspension was extracted with diethyl ether (2×100 ml). The organic portion was dried over sodium sulphate, filtered and concentrated in vacuo to yield the crude N-hydroxy sulfonamide. Purification was achieved by chromatography on silica gel eluting with heptane:ethyl acetate (8:2 v:v) to give the parent compound as a white solid (1.3 g, 44% yield); δH (400 MHz, DMSO) 9.87 (1H, d, 3.4 Hz), 9.39 (1H, d, 3.2 Hz), 7.97 (1H, m), 7.77 (2H, m), 7.68-7.72 (1H, m), 3.83 (3H, s); TR=1.43 min.

Workup

  1. temperaturemaintaining an internal reaction temperature between 5° C. and 15° C
  2. temperatureportionwise maintaining a temperature below 15° C.
  3. concentrationThe resulting suspension was concentrated
  4. customto remove any volatiles
  5. extractionthe aqueous suspension was extracted with diethyl ether (2×100 ml)
  6. dry with materialThe organic portion was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield the crude N-hydroxy sulfonamide
  10. customPurification

Sources & evidence

ORD record
ord-df8fa6c6c7f0483489d116e50186ada8
Source dataset
uspto-grants-2015_08
Patent number
US09115064B2

Reaction notes

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