Sulfamide → 6-nitro-3H-benzo[1,2,3]oxathiazole 2,2-dioxide

HRID 1720027Notes

Reaction equation

HRID 1720027 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[S:12](N)(N)(=[O:14])=[O:13]>COCCOCCOC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][S:12](=[O:14])(=[O:13])[O:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 52471556-nitro-3H-benzo[1,2,3]oxathiazole 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

Diethylene glycol dimethyl ether (350 ml) solution of 2-Amino-5-Nitrophenol (40 g) and sulfamide (25 g) was added dropwise to refluxing diethylene glycol dimethyl ether (100 ml) over a period of 50 minutes. Mixture was stirred and refluxing continued 15 minutes, then cooled to room temperature. Solvent was evaporated off, and 500 ml of 1N hydrochloric acid was added. Reaction mixture was extracted with diethyl ether, extract was dried over magnesium sulfate and solvent was removed in vacuo. Crude product was purified by the column chromatography on silica gel (2% Methanol-Ethyl acetate) to give the desired intermediate, 10.5 g.

Workup

  1. temperaturerefluxing
  2. customSolvent was evaporated off
  3. addition500 ml of 1N hydrochloric acid was added
  4. customReaction mixture
  5. extractionwas extracted with diethyl ether
  6. extractionextract
  7. dry with materialwas dried over magnesium sulfate and solvent
  8. customwas removed in vacuo
  9. customCrude product was purified by the column chromatography on silica gel (2% Methanol-Ethyl acetate)

Sources & evidence

ORD record
ord-7d72b88ecf5b4f87b671297cbc00eff1
Source dataset
uspto-grants-1996_04
Patent number
US05504095

Reaction notes

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