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Pyridine → N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamide

HRID 1081530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081530
[C:1]([C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1)([OH:3])=O.S(Cl)(Cl)=O.[NH2:23][C:24]1[C:25]([OH:43])=[CH:26][C:27]2[C:28]([CH2:40][CH2:41][CH3:42])([CH2:37][CH2:38][CH3:39])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3.N1C=CC=CC=1>O1CCCC1.CN1CCCC1=O>[CH2:40]([C:28]1([CH2:37][CH2:38][CH3:39])[C:27]2[CH:26]=[C:25]([OH:43])[C:24]([NH:23][C:1]([C:4]3[C:5]([O:17][CH3:18])=[CH:6][C:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[O:9][C:8]=4[CH:16]=3)=[O:3])=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:41][CH3:42]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 458266HCID 458266, VerbindungHCID 10540797HCID 10540797, Verbindung

Produkt 1

HCID 10696906N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamideAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Into a 250 ml, 2-necked, round-bottomed flask, equipped with magnetic stirring, nitrogen inlet, and reflux condenser, were placed 6.98 g (28.8 mmole) of 3-carboxy-2-methoxydibenzofuran, 50 ml of dry tetrahydrofuran, 2.20 ml (30.2 mmole) of thionyl chloride, and 0.1 to 0.2 ml of N-methylpyrrolidinone. The mixture was refluxed for 2.5 hours and then allowed to cool to room temperature. Meanwhile, into a 3-necked, 500 ml, round bottomed flask, equipped with magnetic stirring, pressure-equalizing addition funnel, nitrogen inlet, and thermometer, were placed 8.99 g (30.2 mmole) of 3-amino-9,9-dipropyl-2-hydroxyfluorene, 50 ml dry tetrahydrofuran, and 4.77 ml (60.4 mole) of pyridine. To this solution was added the cooled acid chloride over several minutes, resulting in an exotherm and the formation of a precipitate. The mixture was stirred for an additional 1 hour, quenched by pouring into 400 ml of water, and made acidic (pH ≈1). The solid was collected by vacuum filtration, washed with water, slurried in 200 ml of methanol, refiltered, and washed with an additional 100 ml of methanol, resulting in a yellow solid. After drying obtained 10.5 g (70%) of N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamide, mp 252°-255°.

Aufarbeitung

  1. customInto a 250 ml, 2-necked, round-bottomed flask, equipped with magnetic stirring, nitrogen inlet
  2. temperaturereflux condenser
  3. temperatureThe mixture was refluxed for 2.5 hours
  4. customMeanwhile, into a 3-necked, 500 ml, round bottomed flask, equipped with magnetic stirring, pressure-equalizing addition funnel, nitrogen inlet
  5. customresulting in an exotherm
  6. customquenched
  7. additionby pouring into 400 ml of water
  8. filtrationThe solid was collected by vacuum filtration
  9. washwashed with water
  10. washwashed with an additional 100 ml of methanol
  11. customresulting in a yellow solid
  12. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-22f97a073ad3408089d5eb06d8e8aab0
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587112

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