2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → 4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356202

Reaktionsgleichung

Reaktionsgleichung von HRID 356202
[CH2:1]1[CH:10]2[CH:4]([NH:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.[C:16]1(=[O:30])[N:20]([CH2:21][C:22](Cl)=[O:23])[C:19](=[O:25])[C:18]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:17]12.C(=O)([O-])O.[Na+]>ClCCCl>[C:19]1(=[O:25])[N:20]([CH2:21][C:22]([N:5]2[CH:4]3[CH2:3][CH2:2][CH2:1][CH:10]3[C:9](=[O:11])[NH:8][C:7]3[CH:12]=[CH:13][CH:14]=[CH:15][C:6]2=3)=[O:23])[C:16](=[O:30])[C:17]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:18]12

Komponenten

5

Edukt 3

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 189405902,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Produkt 1

HCID 189405414-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (2.02 g, 10 mmol) in 1,2-dichloroethane (15 mL) was added phthalimidoacetyl chloride (2.24 g, 10 mmol),and the mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate (10 mL) to give precipitate, which was filtered off. The aqueous layer of the filtrate was seperated. The organic layer was washed with water, dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was combined with the precipitate filtered previously, which was washed with methanol, followed by recrystallization from chloroform-methanol to give 2.42 g (yield 62%) of a cis-trans mixture (3:2). m.p. 293°-294° C.

Aufarbeitung

  1. customto give precipitate, which
  2. filtrationwas filtered off
  3. customThe aqueous layer of the filtrate was seperated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationsubjected to filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. filtrationfiltered previously
  9. washwhich was washed with methanol
  10. customfollowed by recrystallization from chloroform-methanol

Quellen und Nachweise

ORD-Eintrag
ord-39f1d8aa1d33491e85d71c5964b031c8
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834463

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