Sodium hydride → HCID 178448128, compound

HRID 1419803Notes

Reaction equation

HRID 1419803 reaction equation
[H-].[Na+].[C:3]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)([CH3:5])=[CH2:4].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][N:15]=1.[Cl-].[NH4+]>C1COCC1.C(O)(C)C>[C:3]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:8][CH2:7]1)([CH3:5])=[CH2:4]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 788644-ChloroquinazolineHCID 178448129HCID 178448129, compound

Product 1

HCID 178448128HCID 178448128, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.42 g (17.5 mmol) of NaH (80% pure) was added in portions to a solution of 1.8 g (12.8 mmol) of cis-4isopropenylcyclohexanol in 20 ml of absolute THF. The mixture was then heated at reflux for 3 hours, and a solution of 1.9 g (11.6 mmol) of 4-chloroquinazoline in 10 ml of THF was added dropwise. The reaction mixture was subsequently heated at reflux for 5 hours. After cooling to room temperature, 10 ml of isopropanol were added, the mixture was subsequently stirred for 15 minutes, and the reaction solution was poured into saturated ammonium chloride solution. Extraction was carried out with ether, the combined organic phases were dried over MgSO4 and the solvent was concentrated by evaporation in vacuo. The residue (2.7 g) was purified by flash chromatography over silica gel with petroleum ether/ethyl acetate 3:1. After concentration, 1.8 g (57.6% of theory) were obtained of a colorless oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was subsequently heated
  4. temperatureat reflux for 5 hours
  5. extractionExtraction
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationthe solvent was concentrated by evaporation in vacuo
  8. customThe residue (2.7 g) was purified by flash chromatography over silica gel with petroleum ether/ethyl acetate 3:1
  9. concentrationAfter concentration
  10. custom1.8 g (57.6% of theory) were obtained of a colorless oil

Sources & evidence

ORD record
ord-3e03fbdb49ad43859eaaee978c67eb5d
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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