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

HRID 1348681Notes

Reaction equation

HRID 1348681 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].C(N(C(C)C)C(C)C)C.C1N=CN([S:26](N2C=NC=C2)(=[O:28])=[O:27])C=1>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][S:26](=[O:28])(=[O:27])[O:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 816091,1'-sulphonylbis-1H-imidazoleHCID 49847212-Amino-5-Nitrophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-5-nitrophenol (7.7 g, 50 mmol) in acetonitrile (300 ml) is treated with N-ethyldiisopropylamine (18.7 ml, 110 mmol) and N,N′-sulfuryldiimidazole (10.8 g, 55 mmol) and boiled at reflux for 18 h. After cooling to RT, the solvent is distilled off under reduced pressure, the residue is taken up in 1 N HCl and the product is extracted with ethyl acetate. The product is then purified by flash chromatography (17:2:1, EtOAc/MeOH/H2O).

Workup

  1. temperatureat reflux for 18 h
  2. distillationthe solvent is distilled off under reduced pressure
  3. extractionthe product is extracted with ethyl acetate
  4. customThe product is then purified by flash chromatography (17:2:1, EtOAc/MeOH/H2O)

Sources & evidence

ORD record
ord-ea9838fe2fbf4a42bdb7b16c76c85364
Source dataset
uspto-grants-2007_05
Patent number
US07211592B2

Reaction notes

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