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Acetic Acid → Isohexane ethyl acetate

HRID 2377017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2377017
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[O-:27][C:28]#[N:29].[K+].[C:31]([OH:34])(=[O:33])[CH3:32]>O>[C:31]([O:34][CH2:24][CH3:25])(=[O:33])[CH3:32].[CH3:3][CH2:4][CH2:5][CH:6]([CH3:9])[CH3:7].[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:14]([S:17]([C:20]3[CH:21]=[C:22]([NH:26][C:28]([NH2:29])=[O:27])[CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 21099488HCID 21099488, Verbindung

Produkt 2

HCID 21099528HCID 21099528, VerbindungHCID 21882781Isohexane ethyl acetateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture of [3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]amine hydrochloride (Example 212, 100 mg, 0.26 mmol) and potassium cyanate (63 mg, 0.78 mol) in acetic acid (3 mL) and water (0.5 mL) was stirred at room temperature for 16 hours. The acetic acid was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium hydrogencarbonate solution and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% ethyl acetate/isohexane then 40% ethyl acetate/isohexane, to give the title compound. δH (500 MHz, d6 DMSO): 8.96 (1H, s), 8.13 (1H, s), 7.86 (2H, d, J=8.5 Hz), 7.79 (2H, d, J=8.5 Hz), 7.67 (2H, dd, J=5.6, 8.7 Hz), 7.54-7.52 (1H, m), 7.44-7.40 (3H, m), 7.27 (1H, d, J=16.4 Hz), 7.22 (2H, t, J=8.8 Hz), 5.98 (2H, s).

Aufarbeitung

  1. customThe acetic acid was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 20% ethyl acetate/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-b91a54692a664e17bfb1c392a52c5aaa
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07468393B2

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