Water → HCID 44218926, compound

HRID 474188Notes

Reaction equation

HRID 474188 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-c99ffe9657bc4ad7a591f8f1dc6ddfc1
Source dataset
uspto-grants-2014_01
Patent number
US08637522B2

Reaction notes

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