Sulfuryl chloride → Ethyl 1-(chloromethyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 240349Notes

Reaction equation

HRID 240349 reaction equation
CS[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]1=[O:19].S(Cl)([Cl:23])(=O)=O>ClCCl>[Cl:23][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]1=[O:19]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 68478326HCID 68478326, compound

Product 1

HCID 67533313Ethyl 1-(chloromethyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g (7.5 mmol) of ethyl 1-(methylthiomethyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxy late was dissolved in dichloromethane (10 mL), and 1.3 g (9.8 mmol) of sulfuryl chloride was added dropwise at or below 10° C. The mixture was stirred for 2 hours at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, to obtain ethyl 1-(chloromethyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate. The chloromethylation product thus obtained was used in the subsequent reaction without purification.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f189b639ab254d6f9b5b2d6c0db70b71
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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