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Potassium Carbonate → (S)-4-glycidyloxy-N,N-dimethylbenzo(b)thiophene-2-carboxamide

HRID 460557
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 460557
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15]O)[C:7]=2[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC([N+]([O-])=O)=CC=1)(OC[C@H:29]1[O:31][CH2:30]1)(=O)=O>CN(C=O)C>[CH2:15]([O:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]([N:2]([CH3:17])[CH3:1])=[O:4])[S:9][C:8]=2[CH:10]=[CH:11][CH:12]=1)[C@H:30]1[O:31][CH2:29]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 22729338N,N-dimethyl-4-(hydroxymethyloxy)benzo(b)thiophene-2-carboxamide

Produkt 1

HCID 60078007(S)-4-glycidyloxy-N,N-dimethylbenzo(b)thiophene-2-carboxamideAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of N,N-dimethyl-4-(hydroxymethyloxy)benzo(b)thiophene-2-carboxamide (9.0 g) in DMF (100 ml) was added potassium carbonate (8.0 g), and (S)-glycidyl nosylate (8.0 g) was further added. The mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate to give the title compound (7.5 g).

Aufarbeitung

  1. additionwas further added
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crystals were recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2b67132adc8042ac843d0737ab80b740
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07196199B2

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