Water → HCID 22996551, compound

HRID 1167246Notes

Reaction equation

HRID 1167246 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:6]([CH3:14])[C:5]([Cl:15])=[CH:4][C:3]=1[S:16]([NH2:19])(=[O:18])=[O:17].[O-:20][Mn](=O)(=O)=O.[K+].[OH2:26]>N1C=CC=CC=1>[C:14]([C:6]1[C:5]([Cl:15])=[CH:4][C:3]([S:16]([NH2:19])(=[O:18])=[O:17])=[C:2]([Cl:1])[C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)([OH:20])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 22996563HCID 22996563, compound

Product 1

HCID 22996551HCID 22996551, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2,5-dichloro-4-methyl(morpholino)benzenesulfonamide (773 mg, 2.5 mmol) in pyridine (15 mL) and water (15 mL) at 70° C. was added KMnO4 (1.2 g, 7.50 mmol). The resulting mixture was stirred for 1 h, and then another 500 mg of KMnO4 was added. After stirring at 70° C. overnight, the reaction was filtered via Buchner funnel, washing the precipitated MnO2 with water. The filtrate was diluted with ˜50 mL 1 N NaOH and extracted 4 times with ethyl acetate. The aqueous layer was then acidified with 1 M HCl and extracted twice with ethyl acetate. These second organic extracts were dried and concentrated to provide 4-carboxy-2,5-dichloro (morpholino)benzenesulfonamide (295 mg, 35%) as white crystals. Mass spectrum ES−: 339.8 (M−H).

Workup

  1. stirringAfter stirring at 70° C. overnight
  2. filtrationthe reaction was filtered via Buchner funnel
  3. washwashing the precipitated MnO2 with water
  4. additionThe filtrate was diluted with ˜50 mL 1 N NaOH
  5. extractionextracted 4 times with ethyl acetate
  6. extractionextracted twice with ethyl acetate
  7. customThese second organic extracts were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1cab046ad29e4df0ad0b8e230b242439
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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