Benzenesulfonyl chloride → Ethyl 2-(benzenesulfonamido)-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate

HRID 1506897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506897
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1.O>[C:16]1([S:22]([NH:1][C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Produkt 1

HCID 391240Ethyl 2-(benzenesulfonamido)-4,5,6,7-tetrahydrobenzothiophene-3-carboxylateAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.113 g) was added to a solution of benzenesulphonyl chloride (0.097 g) in pyridine (5 ml) and the resultant solution was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with hydrochloric acid (1M), water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane (5%) to give ethyl 2-benzenesulphonylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.076 g) as a pale yellow solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with hydrochloric acid (1M), water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and pentane (5%)

Quellen und Nachweise

ORD-Eintrag
ord-4e569a7428234ed9a1103146c9171479
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221787B2

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