反応式
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][S:14]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:12][C:11]1[C:2]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[CH:26][CH:27]=2)(=[O:15])=[O:16])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2参加物
反応条件
- 温度
- 135 °C
実験手順
2,3-Dichloroquinoxaline (3.5 g; 17.6 mmol; 1 eq), 4-(aminosulfonyl)-N,N-dimethylbenzamide (4 g; 17.6 mmol; 1 eq) and anhydrous K2CO3 (2.4 g; 17.6 mmol; 1 eq) are taken up in DMA (35 mL) and the resulting suspension is heated at 135° C. for 1 h. After evaporation of the DMA under reduced pressure, the reaction is stopped by addition of water (20 mL) then the suspension is acidified with a 25% aqueous solution of citric acid (70 mL). After overnight standing at 4° C., the yellow precipitate is filtered off, washed several times with water until pH=6 and dried under vacuum at 40° C. overnight affording 5.73 g of a yellow solid. It is taken up in EtOH (25 mL) and the suspension is heated for a few minutes. The precipitate is filtered off and washed twice with EtOH (10 mL) then dried under vacuum at 40° C. overnight to afford 3.96 g (57.6%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 8.27-8.24 (d, J=8.3 Hz, 2H), 7.91 (t, J=7.2 Hz, 2H), 7.79-7.74 (m, 2H), 7.73-7.66 (m, 3H), 3.02 (s, 3H), 2.88 (s, 3H). HPLC (max plot) 95%; Rt 3.18 min. LC/MS: (ES+): 391.3, (ES−): 389.2.
後処理
- customAfter evaporation of the DMA under reduced pressure
- additionthe reaction is stopped by addition of water (20 mL)
- filtrationthe yellow precipitate is filtered off
- washwashed several times with water until pH=6
- customdried under vacuum at 40° C. overnight
出典と根拠
- ORDレコード
- ord-70b4d3424043420e885744456ee2e6ff
- 出典データセット
- uspto-grants-2013_12
- 特許番号
- US08614215B2
関連ノート
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