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Sodium Carbonate → 4-(1-Phenylazulene-2-yl)phenylsulfonamide

HRID 1456831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1456831
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:23]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=[CH:22]3)[C:16]=2C(OC)=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C1(B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]1([C:24]2[C:23]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:15]=2[C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:10][CH:11]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11145169HCID 11145169, Verbindung

Produkt 1

HCID 221071814-(1-Phenylazulene-2-yl)phenylsulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Methyl 2- (4-t-butylaminosulfonylphenyl) -3-phenylazulene-1-carboxylate: To a solution of methyl 3-bromo-2-(4-t-butylaminosulfonylphenyl) azulene-1-carboxlate (0.56 g) in toluene (10.0 ml) was added phenylboronic acid (0.34 g), tetrakis(triphenylphosphine)palladium (0) (0.07 g) and 2M aqueous Na2CO3 (2.3 ml), and the reaction mixture was heated under reflux for 2 hr. The reaction mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20:1) to give the title compound (0.47 g) as violet crystals; mp 76°-77° C.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionby extracted with EtOAc
  4. washThe combined EtOAc extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-253ed14ad9e94e1ca4ec4e3ce1406fe8
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05843999

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