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Hydrochloric Acid → HCID 178427773, Verbindung

HRID 2240017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2240017
Cl.[NH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:5][C:4]=1[CH2:23][S:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].[N:37]([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[C:27]1([S:24]([C:23]2[C:4]3[C:3](=[CH:22][CH:21]=[C:6]([O:7][CH2:8][CH2:9][O:10][S:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)(=[O:12])=[O:13])[CH:5]=3)[NH:2][N:37]=2)(=[O:25])=[O:26])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 58812122Toluene-4-sulfonic acid 2-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-ethyl ester

Produkt 1

HCID 178427773HCID 178427773, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

Ethanol (430 mL) in two portions and 1 N hydrochloric acid (200 mL) were added to toluene-4-sulfonic acid 2-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-ethyl ester (6.5 g, 13 mmol). A solution of sodium nitrite (1.5 g, 22 mmol) in water was then added to the reaction mixture. The reaction was heated to aid in solubility. After stirring at ambient temperature for 2 hours, solid sodium carbonate was added to basic pH. The reaction mixture was stirred at ambient temperature for one hour. It was then solvent evaporated and partitioned in water and ethyl acetate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography with 2% methanol in chloroform. Drying at 63° C. in vacuo yielded toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester a buff-colored foam (3.9 g, 59%); Mass Spectrum (+EI, [M+H]+) m/z 523. 1HNMR (500 MHz, DMSO-d6): δ14.09 (s, 1H), 8.76 (d, 1H, J=8.78 Hz), 8.52-8.55 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.02-8.04 (m, 1H), 7.64-7.74 (m, 3H), 7.55-7.63 (m, 2H), 7.50 (d, 1H, J=9.15 Hz), 7.27 (d, 2H, J=8.05 Hz), 7.14 (d, 1H, J=2.20 Hz), 6.94 (dd, 1H, J=9.15 Hz and 2.44 Hz), 4.32-4.34 (m, 2H), 4.18-4.20 (m, 2H), 2.25 ppm (s, 3H). Elemental Analysis for C26H22N2O6S2: Calcd: C, 59.76; H, 4.24; N, 5.36; Found: C, 59.69; H, 4.28; N, 5.14.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. stirringThe reaction mixture was stirred at ambient temperature for one hour
  3. customsolvent evaporated
  4. custompartitioned in water
  5. washThe organic phase was washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography with 2% methanol in chloroform
  10. customDrying at 63° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e8898a2c33834839b3c984b9c825882a
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723329B2

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