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Sulfuryl chloride → 8-(2-Chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid

HRID 1189815
Notes
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Reaction equation

HRID 1189815 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[C:9]([CH3:28])=[C:10]([C:15]2[C:24]3[N:23]=[CH:22][CH:21]=[N:20][C:19]=3[C:18]([C:25]([OH:27])=[O:26])=[CH:17][CH:16]=2)[CH:11]=[C:12]([CH3:14])[CH:13]=1>CC#N>[Cl:4][C:11]1[C:12]([CH3:14])=[CH:13][C:8]([O:7][CH3:6])=[C:9]([CH3:28])[C:10]=1[C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[N:20][C:19]=2[C:18]([C:25]([OH:27])=[O:26])=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 669145898-(3-Methoxy-2,5-dimethyl-phenyl)quinoxaline-5-carboxylic acid

Product 1

HCID 866411438-(2-Chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acidYield 33.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-5 °C

Procedure

Sulfuryl chloride (29 μL, 0.37 mmol) in CH3CN (1 mL) was added dropwise to a cold (−5° C.) suspension of 8-(3-methoxy-2,5-dimethyl-phenyl)-quinoxaline-5-carboxylic acid (Step 97.1) (113 mg, 0.37 mmol) in CH3CN (4 mL). The reaction mixture was stirred for 10 min at −5° C., quenched by addition of H2O (1 mL) and filtered to afford 42 mg of the title compound as a yellow solid. Title compound: ESI-MS: 343.0 [M+H]+; tR=4.90 min (System 1).

Workup

  1. customquenched by addition of H2O (1 mL)
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b3d8c2ab16794beb84abde875fdc58a3
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08674099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes