Dimethyl Sulfoxide → HCID 86637925, compound

HRID 656491Notes

Reaction equation

HRID 656491 reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[N:12]1[C:21]2[CH2:20][CH2:19][CH2:18][C:17](=[O:22])[C:16]=2[CH:15]=[N:14][CH:13]=1>CCCCC.O1CCCC1.CN(C)C=O.[Cl-].[Na+].O>[N:12]1[C:21]2[CH2:20][CH2:19][CH2:18][C:17]3([CH2:8][O:22]3)[C:16]=2[CH:15]=[N:14][CH:13]=1

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 21859127HCID 21859127, compound

Product 1

HCID 86637925HCID 86637925, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (22 mmol) washed with pentane is admixed under argon with 20 ml of dimethyl sulphoxide. The mixture is heated at 60° C. for an hour and then diluted with 5 ml of tetrahydrofuran. The mixture is cooled to 0° C., a solution of 21 mmol of trimethylsulphonium iodide in 5 ml of N,N-dimethylformamide is added at 0° C., and the mixture is stirred for 10 minutes. A solution of 20 mmol of 7,8-dihydro-6H-quinazolin-5-one [21599-28-0] in 5 ml of N,N-dimethylformamide is added and the reaction mixture is stirred at 20-60° C. for 18 hours. The reaction mixture is poured into cold brine and extracted with tert-butyl methyl ether. The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at 20-60° C. for 18 hours
  3. extractionextracted with tert-butyl methyl ether
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-c92b5ad3001c4a9aa0b80c1e2f7b104f
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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