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

HRID 1271138Notes

Reaction equation

HRID 1271138 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

Conditions

Temperature
25 °C

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 US6159980 (Example 84, Part A), hereby incorporated by reference, and sodium thiomethoxide (701 mg, 10 mol) 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-629bc5f0d0444ca1afa53e3fc37da018
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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