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Hydrochloric Acid → HCID 59249031, compound

HRID 237359
Notes
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Reaction equation

HRID 237359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#N)[CH:26]=2)(=[O:24])=[O:23])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.[OH-:33].[Na+].Cl.C[OH:37]>O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([NH:21][S:22]([C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[C:31]([OH:37])=[O:33])(=[O:24])=[O:23])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 25102201HCID 25102201, compound

Product 1

HCID 59249031HCID 59249031, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8857
Ethyl Acetate
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(3-{[2-chloro-5-(methyloxy)phenyl]amino}quinoxalin-2-yl)-3-cyanobenzenesulfonamide (6.02 g, 12.95 mmol) in methanol (20 mL) and 1,4-dioxane (20 mL) was added 6.0 N aqueous sodium hydroxide (40 mL) at room temperature. The solution was stirred at 90° C. for 3.5 h. The reaction was cooled to room temperature and neutralized slowly by adding 2.0 N hydrochloric acid until the pH of the solution became in the 2-3 range at 0° C. The solution was diluted with ethyl acetate (300 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL) and dried over magnesium sulfate. Filtration and concentration at reduced pressure afforded 3-{[(3-{[2-chloro-5-(methyloxy)phenyl]amino}quinoxalin-2-yl)amino]sulfonyl}benzoic acid (5.921 g, 94%). MS (EI) for C22H17ClN4O5S: 485.0 (MH+)

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custombecame in the 2-3 range at 0° C
  3. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration at reduced pressure

Sources & evidence

ORD record
ord-c1c4ebb59d0e4719bc5ae0ddf724bfe0
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642584B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes