Potassium Carbonate → 4-{[(3-chloroquinoxalin-2-yl)amino]sulfonyl}-N,N-dimethylbenzamide

HRID 1914719Notes

Reaction equation

HRID 1914719 reaction equation
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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 10353728N,N-dimethyl-4-sulfamoylbenzamide

Product 1

HCID 593530404-{[(3-chloroquinoxalin-2-yl)amino]sulfonyl}-N,N-dimethylbenzamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

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.

Workup

  1. customAfter evaporation of the DMA under reduced pressure
  2. additionthe reaction is stopped by addition of water (20 mL)
  3. filtrationthe yellow precipitate is filtered off
  4. washwashed several times with water until pH=6
  5. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-70b4d3424043420e885744456ee2e6ff
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

Loading…