Sodium methanethiolate → 6,7-Dichloro-2, 3-dimethoxy-5-methylthiomethylquinoxaline

HRID 1458594Notes

Reaction equation

HRID 1458594 reaction equation
[CH3:1][S-:2].[Na+].Br[CH2:5][C:6]1[C:15]([Cl:16])=[C:14]([Cl:17])[CH:13]=[C:12]2[C:7]=1[N:8]=[C:9]([O:20][CH3:21])[C:10]([O:18][CH3:19])=[N:11]2>CN(C)C=O>[Cl:16][C:15]1[C:6]([CH2:5][S:2][CH3:1])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:17])[N:11]=[C:10]([O:18][CH3:19])[C:9]([O:20][CH3:21])=[N:8]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxaline

Product 1

HCID 220970456,7-Dichloro-2, 3-dimethoxy-5-methylthiomethylquinoxalineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methanethiolate (22 mg, 0.312 mmol) was added to a stirred solution of 5-bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxaline (see Preparation 28) (100 mg, 0.284 mmol) in dry dimethylformamide (5 ml) under nitrogen at room temperature. The mixture was stirred for 10 minutes and was then quenched with brine and extracted twice with dichloromethane. The combined extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 1:1 hexane:dichloromethane) to give 6,7-dichloro-2, 3-dimethoxy-5-methylthiomethylquinoxaline (79 mg, 87%) as a white solid, m.p. 143°-5° C.

Workup

  1. customwas then quenched with brine
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluting with 1:1 hexane:dichloromethane)

Sources & evidence

ORD record
ord-639e21361ad645be97e0ac43b18e9563
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

Loading…