m-Chloroperbenzoic acid → 2-Sulfamoylfuro[3,2-c]pyridine-5-oxide

HRID 1382986Notes

Reaction equation

HRID 1382986 reaction equation
[S:1]([C:5]1[O:13][C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].ClC1C=CC=C(C(OO)=[O:22])C=1>CO.C(OCC)(=O)C>[S:1]([C:5]1[O:13][C:12]2[CH:11]=[CH:10][N+:9]([O-:22])=[CH:8][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14372124Furo[3,2-c]pyridine-2-sulfonamide

Product 1

HCID 143721302-Sulfamoylfuro[3,2-c]pyridine-5-oxideYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a warm (40° C.) solution of 2-sulfamoylfuro[3,2-c]pyridine (2.68 g, 13.5 mmol) in methanol (30 ml) and ethyl acetate (10 ml) was added dropwise a solution of m-chloroperbenzoic acid (3.22 g, 15 mmol) in ethyl acetate (13 ml). The reaction mixture was stirred for 18 hours as product precipitated. The pure product was collected by filtration and crystallized from hot dimethyl sulfoxide by dilution with ethanol to give 2.4 g (83% yield), m.p. 247°-248° C.

Workup

  1. customprecipitated
  2. filtrationThe pure product was collected by filtration
  3. customcrystallized from hot dimethyl sulfoxide by dilution with ethanol
  4. customto give 2.4 g (83% yield), m.p. 247°-248° C.

Sources & evidence

ORD record
ord-9e64870d66ed47cd91d6e226ac95e6d4
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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