Hydrochloric Acid → HCID 59088004, Verbindung

HRID 656282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656282
[N:1]1([CH2:7][CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.O.NN.Cl.[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][N:33]=[C:34]=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>CO.O1CCCC1.CN(C)C=O.ClCCl.C(N(CC)CC)C>[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][NH:33][C:34]([NH:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 144473502-[2-(Thiomorpholin-4-yl)ethyl]-1H-isoindole-1,3(2H)-dioneHCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzene

Produkt 1

HCID 59088004HCID 59088004, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2-(2-thiomorpholin-4-ylethyl)isoindol-1,3-dione 15-1 (2.76 g) was dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml) and to the solution was added dropwise hydrazine hydrate (550 mg), followed by stirring for 21 hours. To the obtained solution was added 2 N aqueous hydrochloric acid solution (6 ml), and the mixture was stirred for 3 hours and then concentrated under reduced pressure. To the concentrate was added water (15 ml) and the undissolved material was filtered off. The filtrate was concentrated to obtain reaction mixture (1.62 g) as a solid. The obtained mixture (150 mg) was dissolved in dimethylformamide (5 ml) and to the solution was added 4-t-butylbenzylisothiocyanate (210 mg) and a small amount of triethylamine, followed by stirring at room temperature for 23 hours. The resulting mixture was diluted with dichloromethane, washed with water, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the concentrate was added water (15 ml)
  4. filtrationthe undissolved material was filtered off
  5. concentrationThe filtrate was concentrated
  6. customto obtain
  7. stirringby stirring at room temperature for 23 hours
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-1e55c4e29a5947fabbbbb06a7c0ccc94
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071650B2

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