HCID 19806718, compound → HCID 19806666, compound

HRID 1681473Notes

Reaction equation

HRID 1681473 reaction equation
[CH2:1]([O:3][C:4]1[C:8]([Br:9])=[C:7]([C:10](=[O:12])N)[S:6](=[O:13])[N:5]=1)[CH3:2].N([O-])=[O:15].[Na+]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]1[C:8]([Br:9])=[C:7]([C:10]([OH:15])=[O:12])[S:6](=[O:13])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 19806718HCID 19806718, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19806666HCID 19806666, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Ethoxy-4-bromo-5-carbamoylisothiazole-1-oxide (267 mg, 1.0 mmol) was dissolved in 2 ml of trifluoroacetic acid and sodium nitrite (138 mg, 2.0 mmol) was added in small portions over a two minute period with stirring. Stirring was continued for two minutes at room temperature and then the solvent was removed in vacuo. The residual gum was stirred in 5 ml of ice water for five minutes. Filtration gave 174 mg (65% yield) of yellow solid; mp 158°-160° C., dec.

Workup

  1. stirringStirring
  2. customthe solvent was removed in vacuo
  3. stirringThe residual gum was stirred in 5 ml of ice water for five minutes
  4. filtrationFiltration

Sources & evidence

ORD record
ord-927787ca1f154d5596a3dde4c6d28e5a
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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