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

HRID 331192

反応式

HRID 331192 の反応式
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[C:22](Cl)=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[C:22]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)(=[O:9])=[O:10])=[N:21][C:20]2[C:15]([N:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 1509243-Fluorobenzenesulfonamide

生成物 1

HCID 57625365N-(3-chloroquinoxalin-2-yl)-3-fluorobenzenesulfonamide収率 84.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

3-fluorobenzenesulfonamide (250 mg, 1.4 mmol), 2,3-dichloroquinoxaline (284.1 mg, 1.4 mmol) and dry K2CO3 (198.4 mg, 1.4 mmol) are dissolved in dry DMF (0.8 ml) and heated up to 135° C. in a sealed tube for 2.5 h. When TLC confirms the completion of the reaction, the reaction mixture is cooled down to rt and quenched by addition of water (4 ml) and AcOH (0.03 ml). The residue obtained is triturated and the resulting solid is filtered and washed with water until neutral pH then dried under vacuum to afford 400 mg (83%) of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 12.8-10.9 (br s, 1H), 8.05-7.62 (m, 7H), 7.54 (td, J=2.0, 8.5 Hz, 1H). HPLC (max plot) 94%; Rt 3.79 min. LC/MS: (ES+): 338.1, (ES−): 336.1.

後処理

  1. customthe completion of the reaction
  2. temperaturethe reaction mixture is cooled down to rt
  3. customquenched by addition of water (4 ml) and AcOH (0.03 ml)
  4. customThe residue obtained
  5. customis triturated
  6. filtrationthe resulting solid is filtered
  7. washwashed with water until neutral pH
  8. customthen dried under vacuum

出典と根拠

ORDレコード
ord-c3076cf4b3dc4172a67b7cbff330ec16
出典データセット
uspto-grants-2014_11
特許番号
US08877757B2

関連ノート

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