1,2-Dichloroethane → HCID 11772511, Verbindung

HRID 272577

Reaktionsgleichung

Reaktionsgleichung von HRID 272577
[OH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[CH3:21][N:22]([CH3:27])[CH2:23][C:24](O)=[O:25].C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:20]=[C:17]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[O:13][C:14]4[CH:15]=[CH:16][C:3]([CH2:2][O:1][C:24](=[O:25])[CH2:23][N:22]([CH3:27])[CH3:21])=[CH:4][C:5]=4[C:6]([C:7]=23)=[N:19][NH:18]1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 673N,N-DimethylglycineHCID 1145979210-Hydroxymethyl-2H-7-oxa-1,2-diaza-benzo[de]anthracen-3-one

Produkt 1

HCID 11772511HCID 11772511, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 57 (0.5 mmol) in anhydrous DMF was added dimethyl glycine (0.75 mmol) and EDC (0.75 mmol) and DMAP (catalytic amount). The reaction mixture was stirred at room temperature overnight. Solvent was removed in vacuo. To the residue, 100 mL of ethyl acetate was added. The organic layer was washed with water, and brine, then dried with MgSO4. The Solvents were removed to afford a colorless oil, which was recrystallized in EtOAc/Hexanes to afford an off-white solid 59 in 30% yield. MS (ES+): 352; MP: 227-230° C.; 1H-NMR (CDCl3, 400 MHz): 10.15 (s, 1H), 8.14 (d, J=2.0 Hz, 1H), 8.06 (dd, J=8.0 and 1.0 Hz, 1H), 7.80 (t, J=8.0 Hz, 1H), 7.53 (dd, J=8.0 and 1.0 Hz, 1H), 7.47 (dd, J=8.5 and 2.0 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 5.21 (s, 2H), 3.26 (s, 2H), 2.37 (s, 6H); Anal. Calcd. for C19H17N3O4: C, 64.95; H, 4.86; N, 11.96. Found: C, 64.95; H, 4.78; N, 12.14.

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. additionTo the residue, 100 mL of ethyl acetate was added
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried with MgSO4
  5. customThe Solvents were removed
  6. customto afford a colorless oil, which
  7. customwas recrystallized in EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4022b2dde6a349a4a70c4511401bf191
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456178B2

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