HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 331193
Notes
Print preview

Reaction equation

HRID 331193 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.[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-079c40edb76b49d1abd5d71b77b97614
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877757B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes