4-Nitrobenzenesulfonyl chloride → 4-Nitrobenzenesulfonic Acid 2-[3-(Tritylamino)phenyl]ethyl Ester

HRID 1097021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097021
[C:1]([NH:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][OH:29])[CH:24]=[CH:25][CH:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([NH:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][O:29][S:47]([C:44]2[CH:43]=[CH:42][C:41]([N+:38]([O-:40])=[O:39])=[CH:46][CH:45]=2)(=[O:48])=[O:49])[CH:24]=[CH:25][CH:26]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 9237DabcoHCID 516892Sodium BicarbonateHCID 667703302-[3-(Tritylamino)phenyl]ethanol

Produkt 1

HCID 866469604-Nitrobenzenesulfonic Acid 2-[3-(Tritylamino)phenyl]ethyl EsterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-[3-(tritylamino)phenyl]ethanol (5.00 g, 13.2 mmol) and triethylenediamine (2.22 g, 19.8 mmol) in DCM (52.7 mL) under nitrogen at 0° C. was added portion-wise p-nitrobenzenesulfonyl chloride (3.50 g, 15.8 mmol) over a period of 5 min. The resulting mixture stirred at 0° C. for 40 min and then saturated aqueous sodium bicarbonate solution (˜50 mL) was added. The mixture was stirred at room temperature for 10 min and then the layers were separated. The aqueous layer was extracted with DCM (2ט50 mL) and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (7.44 g, 100% yield) as an orange-yellow foamy solid.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 10 min
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (2ט50 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aadb382e10734f85820bf0de496ef181
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138345B2

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