Water → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-propionyloxymethylcarbamate

HRID 1597814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597814
N1C=CC=CC=1.[C:7](Cl)(=[O:10])[CH2:8][CH3:9].[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:34][OH:35])[C:30](=[O:33])[O:31][CH3:32])=[C:25]([CH3:36])[CH:24]=1.O>C(Cl)Cl>[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:34][O:35][C:7](=[O:10])[CH2:8][CH3:9])[C:30](=[O:33])[O:31][CH3:32])=[C:25]([CH3:36])[CH:24]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 62324Propionyl chlorideHCID 18932060Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamate

Produkt 1

HCID 18932176Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-propionyloxymethylcarbamateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.1 ml of pyridine and 0.1 ml of propionyl chloride were added to a solution of 121 mg of methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamate (prepared as described in Example 19 above) in 2 ml of methylene chloride cooled in an ice-water bath and the resulting mixture was stirred at the same temperature for 10 minutes. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude residue which was purified by column chromatography through silica gel using a 5:1 by volume mixture of hexane and ethyl acetate to give 133 mg (yield 94%) of the title compound as an oil.

Aufarbeitung

  1. temperaturecooled in an ice-water bath
  2. extractionthe resulting mixture was extracted with methylene chloride
  3. extractionThe resulting extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. customto give a crude residue which
  8. customwas purified by column chromatography through silica gel using a 5:1
  9. additionby volume mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a480c3a1d635434893a84d1af1fc6b09
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736487

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