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

HRID 331193

반응식

HRID 331193 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-079c40edb76b49d1abd5d71b77b97614
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877757B2

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