Methanesulfonic Acid → 1-(3,5-Dioxapiperidin-1-yl)sulphonyl-4-nitrobenzene

HRID 1792761Notes

Reaction equation

HRID 1792761 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:14]1[CH2:19]O[CH2:17][O:16][CH2:15]1.CS(O)(=O)=O>C(O)(=O)C.O>[N:13]1([S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[CH2:17][O:16][CH2:15][O:14][CH2:19]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80811,3,5-TrioxaneHCID 227844-Nitrobenzenesulfonamide

Product 1

HCID 220249211-(3,5-Dioxapiperidin-1-yl)sulphonyl-4-nitrobenzeneYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrobenzenesulphonamide (2.02 g, 10 mmol) was added to a solution of 1,3,5-trioxane (1.96 g, 20 mmol) in acetic acid (5 ml). The mixture was stirred for 5 minutes and methanesulphonic acid (10 ml) was added slowly. The mixture was then stirred at 35° C. for 20 minutes, cooled to 0° C., diluted with water and extracted with ethyl acetate. The combined extracts were washed twice with water and twice with 5% aqueous sodium hydrogen carbonate solution, and then dried and the volatiles removed by evaporation. The residue was recrystallized from ethanol to give the title compound (955 mg, 35% yield). NMR: 4.87 (s, 2H), 5.30 (s, 4H), 8.20 (d, 2H), 8.42 (d, 2H).

Workup

  1. stirringThe mixture was then stirred at 35° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed twice with water and twice with 5% aqueous sodium hydrogen carbonate solution
  4. customdried
  5. customthe volatiles removed by evaporation
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9b3103b72e3147378a37f482c253d6ca
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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