Potassium Carbonate → HCID 10727486, compound

HRID 1189716Notes

Reaction equation

HRID 1189716 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][OH:9].Cl[S:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])(=[O:13])=[O:12].S(Cl)(Cl)(=O)=O>O.CO.C1COCC1>[OH:9][NH:8][S:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])(=[O:13])=[O:12]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 10727486HCID 10727486, compoundYield 267.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium carbonate (0.43 g, 3.10 mmol) in water (1.2 ml) was added drop wise to a solution of hydroxylamine hydrochloride (0.21 g, 3.10 mmol) in water (0.8 ml) at 0° C. maintaining an internal reaction temperature between 5° C. and 15° C. THF (4 ml) and methanol (1 ml) were added, followed by 3-chlorosulfonyl-benzoic acid (0.34 g, 1.55 mmol) portion wise 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 LCMS. The resulting suspension was concentrated to remove any volatiles and the aqueous suspension was extracted with diethyl ether (2×100 ml), and the combined organic layers were discarded. The aqueous layer was acidified to pH=1, adding a solution of hydrochloric acid (2N) drop wise, then extracted with diethyl ether (2×100 ml). The organic portion was dried over sodium sulphate, filtered and concentrated in vacuo to yield the clean N-hydroxysulphonamide as a yellow solid (0.9 g, 27% yield); δH (400 MHz, DMSO) 13.52 (1H, br. s.), 9.72-9.74 (2H, m), 8.38 (1H, t, 1.6 Hz), 8.23 (1H, ddd, 7.9, 1.3, 1.2 Hz), 8.06 (1H, ddd, 7.8, 2.0, 1.2 Hz), 7.77 (1H, t, 7.7 Hz); TR=1.19 min.

Workup

  1. temperaturemaintaining an internal reaction temperature between 5° C. and 15° C
  2. temperaturewise 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. additionadding a solution of hydrochloric acid (2N) drop wise
  7. extractionextracted with diethyl ether (2×100 ml)
  8. dry with materialThe organic portion was dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf37da4cae694fec992c6be8952bee04
Source dataset
uspto-grants-2014_03
Patent number
US08674132B2

Reaction notes

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