Diethyl Pyrocarbonate → HCID 18918954, compound

HRID 1291354Notes

Reaction equation

HRID 1291354 reaction equation
[C:1]([C:4]1[CH:32]=[CH:31][C:7]([C:8]([C:10]2[CH:30]=[CH:29][C:13]([CH2:14][S:15][C:16]3[N:25]([CH3:26])[C:24](=[O:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[CH3:28])[N:17]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].CCOC(OC(OCC)=O)=O.[CH3:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C>[CH3:26][N:25]1[C:24](=[O:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:28])[N:17]=[C:16]1[S:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([C:1]([N:48]3[CH2:49][CH2:50][N:45]([CH3:44])[CH2:46][CH2:47]3)=[O:2])=[CH:32][CH:31]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 531671-MethylpiperazineHCID 18918934HCID 18918934, compound

Product 1

HCID 18918954HCID 18918954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(4-carboxybenzoyl)benzyl]thio-3,5-dimethyl-4(3H)-quinazolinone (0.320 g, 0.720 mmol) in DMF (5.0 ml) were added DEPC (0.37 g, 2.27 mmol) and 1-methylpiperazine (0.200 ml, 1.80 mmol) and the mixture was stirred at room temperature overnight. The solvent was then distilled off and the residue was dissolved in ethyl acetate and washed with saturated aqueous NaCl solution. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride: methanol: ammonia=20:1:0.1). The resulting solid was recrystallized from ethanol to provide colorless needles.

Workup

  1. distillationThe solvent was then distilled off
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride: methanol: ammonia=20:1:0.1)
  7. customThe resulting solid was recrystallized from ethanol
  8. customto provide colorless needles

Sources & evidence

ORD record
ord-7f28d6aadaaf4b0c92c1858b92b17b45
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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