Acetate → HCID 13123247, compound

HRID 2399696Notes

Reaction equation

HRID 2399696 reaction equation
C([S:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O)C1C=CC=CC=1.Cl.[NH2:20]O.C([O-])(=O)C.O>C(O)C>[CH3:18][O:17][C:16]1[C:9]2[S:8][N:20]=[CH:11][C:10]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 175AcetateHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 19384357HCID 19384357, compound

Product 1

HCID 13123247HCID 13123247, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 2-benzylthio-3-methoxybenzaldehyde are dissolved in 40 ml of ethanol, and 3.9 g of hydroxylamine hydrochloride are added. 40 ml of acetate buffer (pH=5) are added to this solution, and the mixture is stirred for 30 minutes at room temperature. The mixture is poured into water and extracted using ethyl acetate. The organic phase is washed using saline, dried over sodium sulfate, filtered and concentrated. The resulting oil is added to a suspension of 1.6 g of phosphorus pentoxide in20 ml of methanesulfonic acid, and the mixture is stirred overnight at room temperature. The reaction mixture is poured onto ice and extracted using ethyl acetate. The organic phase is washed with saturated sodium hydrogen carbonate solution and with saline and dried over sodium sulfate, filtered and concentrated. After purification by chromatography, 7-methoxybenzisothiazole is obtained in the form of an oil.

Workup

  1. extractionextracted
  2. washThe organic phase is washed
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe resulting oil is added to a suspension of 1.6 g of phosphorus pentoxide in20 ml of methanesulfonic acid
  7. stirringthe mixture is stirred overnight at room temperature
  8. additionThe reaction mixture is poured onto ice
  9. extractionextracted
  10. washThe organic phase is washed with saturated sodium hydrogen carbonate solution and with saline
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customAfter purification by chromatography

Sources & evidence

ORD record
ord-8f3d905014ee441f924c1fd60661ec0e
Source dataset
uspto-grants-1995_09
Patent number
US05451595

Reaction notes

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