1-Pentanol → HCID 14424736, compound

HRID 2352511Notes

Reaction equation

HRID 2352511 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[CH2:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19]>CN(C)C=O>[Cl:1][C:2]1[N:11]=[C:10]([O:20][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 62761-PentanolHCID 24758Sodium hydrideHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 14424736HCID 14424736, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

7.3 g of 2,4-dichloroquinazoline (J. Chem. Soc., 1947, 775) was suspended in 40 ml of N,N-dimethylformamide, and with ice cooling, 1.9 g of sodium hydride (oily, 60 %) was added. A solution of 3.7 g of l-pentanol in 5 ml of N,N-dimethylformamide was added dropwise over 5 minutes, and then further stirred at 50° C. for 1 hour. After cooling, the reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was subjected to silica gel column chromatography [eluted with hexane/ethyl acetate (8:1, v/v)] to give 8 g of 2-chloro-4-pentyloxyquinazoline. A portion of this produce was recrystallized from hexane to give a product having the following physical property values.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane/ethyl acetate (8:1

Sources & evidence

ORD record
ord-b111351a28f54dc880bbf6cd1412e5b4
Source dataset
uspto-grants-1989_10
Patent number
US04877790

Reaction notes

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