Sodium Carbonate → HCID 69354035, compound

HRID 1271294Notes

Reaction equation

HRID 1271294 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([SH:19])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:26]([O:30][C:31](=[O:39])[CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37]Br)([CH3:29])([CH3:28])[CH3:27]>CC(C)=O>[C:26]([O:30][C:31](=[O:39])[CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][S:19][C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:11]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 86592459Tert-butyl (4-bromobutyloxy)acetateHCID 178527736HCID 178527736, compound

Product 1

HCID 69354035HCID 69354035, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 500 mg of 5,6-diphenyl-2-pyrazinethiol in 20 ml of acetone, 321 mg of sodium carbonate was added and a solution of 556 mg of 2-(4-bromobutyloxy)acetic acid tert-butyl ester in 2 ml of acetone was added dropwise while stirring under ice-cooling, followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and then the residue was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 701 mg of the desired compound as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 24 hours
  3. customThe solvent was evaporated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af372978f39e4dca808c632b52ae72e2
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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