Water → HCID 44218926, compound

HRID 512108Notes

Reaction equation

HRID 512108 reaction equation
[SH:1][C:2]1[C:3](=[O:11])[N:4]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:1][C:2]2[C:3](=[O:11])[N:4]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:6][N:7]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 178456399HCID 178456399, compound

Product 1

HCID 44218926HCID 44218926, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (2.30 mM) of 3-mercapto-1-propylpyrazin-2(1H)-one, 319.2 μl (1.21 mM) of 4-chlorobenzylbromide and 637 mg (4.6 mM) of potassium carbonate in 4 ml of tetrahydrofurane were stirred overnight at room temperature. Water was added and the aqueous layer was extracted with ethyle acetate. The organic layer was separated and washed with water, dried on anhydrous sodium sulfate and evaporated under vacuum, to give an oil which was purified by silica gel column chromatography, using dichloromethane/dimethylketone (98/2) as eluant, to give 600 mg of 3-[(4-chlorobenzyl)thio]-1-propylpyrazin-2(1H)-one. Yield: 88%.

Workup

  1. extractionthe aqueous layer was extracted with ethyle acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated under vacuum
  6. customto give an oil which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f23a695abeb6452b9f17f3203e280d7b
Source dataset
uspto-grants-2015_08
Patent number
US09102632B2

Reaction notes

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