Sodium methanethiolate → 5-bromo-1-(1-ethylpropyl)-3-(methylthio)-2 (1H)-pyrazinone

HRID 2251003Notes

Reaction equation

HRID 2251003 reaction equation
Br[C:2]1[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:15][S-:16].[Na+]>C1COCC1.O.C(OCC)(=O)C>[Br:8][C:6]1[N:7]=[C:2]([S:16][CH3:15])[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=1

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 220043223,5-dibromo-1-(1-ethylpropyl)-2(1H)-pyrazinone

Product 1

HCID 588451705-bromo-1-(1-ethylpropyl)-3-(methylthio)-2 (1H)-pyrazinoneYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dibromo-1-(1-ethylpropyl)-2(1H)-pyrazinone (XXX) (3.23 g, 10 mmol), prepared using the conditions described in U.S. Pat. No. 6,159,980 (Example 84, Part A), hereby incorporated by reference, and sodium thiomethoxide (701 mg, 10 mmol) in THF (50 mL) was stirred at 25° C. for 72 h. The reaction mixture was diluted with water (75 mL) and ethyl acetate (75 mL). The organic phase was dried over (MgSO4), filtered, and concentrated in vacuo to give crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexane 1:4) gave the product XXXI (2.30 g, 82%) as a white solid.

Workup

  1. dry with materialThe organic phase was dried over (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto give crude residue
  5. customPurification by flash column chromatography (silica, ethyl acetate:hexane 1:4)

Sources & evidence

ORD record
ord-1ff270b30fb4462ba812792764683a6b
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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