Hydrogen Peroxide → N2-(2-chlorophenyl)-N2-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,9-dicarboxamide

HRID 627853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627853
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:27])[C:9]([C:11]1[S:26][C:14]2[C:15]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:13]=2[CH:12]=1)=[O:10].C([O-])([O-])=[O:29].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:27])[C:9]([C:11]1[S:26][C:14]2[C:15]3[CH:23]=[C:22]([C:24]([NH2:25])=[O:29])[CH:21]=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:13]=2[CH:12]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 44242168N-(2-chlorophenyl)-9-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Produkt 1

HCID 56833738N2-(2-chlorophenyl)-N2-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,9-dicarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a mixture of N-(2-chlorophenyl)-9-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide 120 (120 mg) and K2CO3 (49 mg) in dry DMSO (2 mL) was added 33% hydrogen peroxide (40 μL). The resultant was stirred overnight at room temperature. Ice was added to the resulting solution and the solid formed was collected, washed with water and dried to give 119. NMR: (CDCl3): 3.04 (t, 2H, CH2, J=5.02 Hz), 3.42 (s, 3H, CH3), 4.28 (t, 2H, CH2, J=5.06 Hz), 5.75 (sbr, 2H, NH2), 6.71 (s, H, ArH), 7.03 (d, H, ArH, J=8.44 Hz), 7.39-7.45 (m, 3H, 3×ArH), 7.55-7.60 (m, 2H, 2×ArH), 7.99 (d, H, ArH, J=1.81 Hz). MS: (ESI+) MH+ 413.14

Aufarbeitung

  1. additionIce was added to the resulting solution
  2. customthe solid formed
  3. customwas collected
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a366675f83cd4911a4a3195173ef5d01
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309265B2

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