Potassium Carbonate → N-(3-chloroquinoxalin-2-yl)-3-methylbenzenesulfonamide

HRID 655620

反応式

HRID 655620 の反応式
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.[CH3:13][C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:12][C:11]1[C:2]([NH:23][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([CH3:13])[CH:15]=2)(=[O:21])=[O:22])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 74697m-Toluenesulphonamide

生成物 1

HCID 4200291N-(3-chloroquinoxalin-2-yl)-3-methylbenzenesulfonamide収率 65.7%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
170 °C

実験手順

A suspension of 2,3-dichloroquinoxaline (500 mg; 2.5 mmol; 1 eq), 3-methylbenzene sulfonamide (430.1 mg, 2.5 mmol, 1 eq.), dry K2CO3 (347.2 mg, 2.5 mmol, 1 eq.) in DMA (5 ml) is heated up at 170° C. in the microwave for 30 min under normal absorption. The solvent is evaporated to dryness. Water (20 ml) is added then AcOH until acidic pH. The residual suspension is left at 4° C. for 1 h and the precipitate formed is filtered off, washed with water until neutral, then ACN and dried under vacuum at 40° C. overnight, to afford 548.3 mg (65%) of the title compound. 1H NMR (DMSO-d6) δ 11.53 (brs, 1H), 7.99 (m, 2H), 7.87 (t, J=8.6 Hz, 2H), 7.77 (dt, J=1.5, 7.5 Hz, 1H), 7.67 (t, J=8.0 Hz, 1H), 7.56-7.43 (m, 2H), 2.42 (s, 3H). HPLC (max plot) 99%; Rt 3.70 min. LC/MS: (ES+): 334.2, (ES−): 332.2.

後処理

  1. customThe solvent is evaporated to dryness
  2. additionWater (20 ml) is added
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water until neutral, then ACN
  6. customdried under vacuum at 40° C. overnight

出典と根拠

ORDレコード
ord-4f079997fb154167b50a705493d75b56
出典データセット
uspto-grants-2011_12
特許番号
US08071597B2

関連ノート

読み込み中…