Potassium Carbonate → 4-[(4-Methylphenyl)sulfonyl]-9-nitro-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

HRID 1089545Notes

Reaction equation

HRID 1089545 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]([CH2:36][CH2:37]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:23][CH2:24][O:8][C:7]3[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[O:11][CH2:37][CH2:36]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 267409N,N-bis(2-(p-toluenesulfonyloxy)ethyl)-p-toluenesulfonamideHCID 35051094-Nitrocatechol

Product 1

HCID 148563554-[(4-Methylphenyl)sulfonyl]-9-nitro-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To dimethylformamide (200 mL) add 4-nitrocatechol (13.8 g, 89 mmol), 4-methyl-N,N-bis[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]benzenesulfonamide (50.7 g, 89.4 mmol), and K2CO3 (27 g, 0.19 mol). Stir and heat the reaction at 110° C. Monitor the progress of the reaction by thin-layer chromatography. Upon completion remove the heat and add water (1.3 L) and methanol (300 mL). Collect the precipitate on paper by suction filtration. Wash the solid with water (2 L). Chromatograph the material on silica (300 g) with CH2Cl2 to obtain the title compound.

Workup

  1. temperatureheat
  2. customthe reaction at 110° C
  3. customMonitor the progress of the reaction by thin-layer chromatography
  4. customUpon completion remove the
  5. temperatureheat
  6. additionadd water (1.3 L) and methanol (300 mL)
  7. customCollect the precipitate on paper
  8. filtrationby suction filtration
  9. washWash the solid with water (2 L)

Sources & evidence

ORD record
ord-b8b68b4a029d40cca1a79aeddaa89174
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

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