Ethyl benzoylformate → 1-[2-(Benzylthio)-8-oxo-5,6,7,8-tetrahydroquinazolin-7-yl]-2-phenylethane-1,2-dione

HRID 44615

Reaction equation

HRID 44615 reaction equation
[CH2:1]([S:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:19])[C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:22]=[C:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24](OCC)=[O:25]>O1CCCC1>[CH2:1]([S:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH:13]([C:24](=[O:25])[C:23]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:22])[C:12](=[O:19])[C:11]=2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15349Ethyl benzoylformateHCID 24758Sodium hydrideHCID 574441132-(benzylthio)-6,7-dihydroquinazolin-8(5H)-one

Product 1

HCID 574441141-[2-(Benzylthio)-8-oxo-5,6,7,8-tetrahydroquinazolin-7-yl]-2-phenylethane-1,2-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.22 g (0.81 mmol) of 2-(benzylthio)-6,7-dihydroquinazolin-8(5H)-one in 5 mL of dry tetrahydrofuran cooled to −50° C., 0.10 g of sodium hydride 60% in mineral oil were added. The resulting suspension was maintained at the same temperature for 30 minutes and then 0.59 mL of ethyl α-oxobenzeneacetate (PhCOCOOEt) were added and the reaction mixture allowed to come to room temperature. After 16 hours the mixture was partitioned between water and ethyl acetate and the organic layer was dried over Na2SO4 and evaporated to dryness. The residue was purified by chromatography on a silica gel column (eluant hexane/ethyl acetate 7/3) giving 0.22 g (68% yield) of the title compound.

Workup

  1. temperatureThe resulting suspension was maintained at the same temperature for 30 minutes
  2. customto come to room temperature
  3. customAfter 16 hours the mixture was partitioned between water and ethyl acetate
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on a silica gel column (eluant hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-6cb9fd63185241d28ffc6683e788d26e
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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