Sodium methanethiolate → HCID 66746858, compound

HRID 2279401Notes

Reaction equation

HRID 2279401 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:13][S-:14].[Na+]>CN1CCCC1=O>[CH3:13][S:14][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 49132647-bromo-1H-quinoxalin-2-one

Product 1

HCID 66746858HCID 66746858, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 7-bromo-1H-quinoxalin-2-one (12.0 g, 53.3 mmol, 1.0 eq) and sodium methanethiolate (9.44 g, 133.3 mmol, 2.5 eq) in N-methylpyrrolidone is stirred at 160° C. for 1 hour. Then solvent is evaporated and the residue is dissolved in water, acidified to pH=5 with 20% hydrochloric acid aqueous solution at 0° C., and the resulting precipitate is collected by filtration, washed with water and ethyl acetate to afford 7-methylsulfanyl-1H-quinoxalin-2-one as a yellow solid (9.23 g, 54% yield).

Workup

  1. customThen solvent is evaporated
  2. dissolutionthe residue is dissolved in water
  3. customacidified to pH=5 with 20% hydrochloric acid aqueous solution at 0° C.
  4. filtrationthe resulting precipitate is collected by filtration
  5. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-d40d66ead3804036adebf46a47cef331
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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