Acetic Acid → HCID 25027942, compound

HRID 1669954Notes

Reaction equation

HRID 1669954 reaction equation
Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:21])[CH3:20].C(O)(=O)C.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:43]=[C:44]([O:46][CH3:47])[CH:45]=1)[NH2:42]>CO.O>[CH3:47][O:46][C:44]1[CH:43]=[C:41]([NH:42][C:2]2[C:11]([NH:32][S:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[CH:28][CH:27]=3)(=[O:30])=[O:31])=[N:10][C:9]3[C:4]([N:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:40]=[C:39]([O:38][CH3:37])[CH:45]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 663013,5-DimethoxyanilineHCID 17817955BenzenesulfonaMide, 4-(1-Methylethoxy)-

Product 1

HCID 25027942HCID 25027942, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A solution of 2,3-dichloroquinoxaline (2.0 mL, 0.38 M) was combined with K2CO3 (105 mg, 0.76 mmol) in a glass vial. A solution of 4-isopropoxybenzene sulfonamide (1.75 mL, 0.43 M) was added and the solution was stirred overnight at 125° C. After cooling, acetic acid (45 mL, 0.79 mmol) and 3,5-dimethoxyaniline (230 mg, 1.5 mmol) were added. The reaction mixture was stirred again at 125° C. overnight. Upon cooling, the reaction mixture was diluted with 8 mL of methanol and then 8 mL of water. The precipitate was collected by filtration and recrystallized from N,N-dimethylacetamide/water to give N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)-4-isopropoxy-benzenesulfonamide (45 mg, 12%). 1H-NMR (400 MHz, d6-DMSO): 12.16 (bs, 1H), 8.93 (s, 1H), 8.03 (d, 2H), 7.92 (bs, 1H), 7.56 (d, 1H), 7.36 (m, 4H), 7.07 (d, 2H), 6.24 (s, 1H), 4.72 (m, 1H), 3.76 (s, 6H), 1.27 (d, 6H); MS (EI) m/z C25H26N4O5S: 495 (MH+).

Workup

  1. temperatureAfter cooling
  2. stirringThe reaction mixture was stirred again at 125° C. overnight
  3. temperatureUpon cooling
  4. filtrationThe precipitate was collected by filtration
  5. customrecrystallized from N,N-dimethylacetamide/water

Sources & evidence

ORD record
ord-7ba110ee58af408b80ff450c7c2de2c9
Source dataset
uspto-grants-2011_08
Patent number
US07989622B2

Reaction notes

Loading…