Isopropanol → HCID 15279354, compound

HRID 234639Notes

Reaction equation

HRID 234639 reaction equation
[H-].[Na+].[CH:3](=[C:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][N:18]=1.C(O)(C)C>C1COCC1.[NH4+].[Cl-].CCOCC>[CH:3](=[C:9]1[CH2:14][CH2:13][CH:12]([O:15][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH2:11][CH2:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 15279353HCID 15279353, compound

Product 1

HCID 15279354HCID 15279354, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 19379374HCID 19379374, compoundSolvent

Procedure

130 mg (4.3 mmol) of 80% NaH are added to a solution of 0.7 g (3.5 mmol) of 4-hexylidenecyclohexanol in 20 ml of absolute THF, and the mixture is refluxed for 1 hour until deproteination is complete. 0.6 g (3.6 mmol) of 4-chloroquinazoline is subsequently added to the reaction solution at boiling point, and the mixture is refluxed for 3 hours. For working up, 2 ml of isopropanol are added. After cooling, the mixture is taken up in aqueous NH4Cl/ether and the organic phase is dried over MgSO4. Concentration of the solvent gives 1.1 g (crude product which is purified by flash chromatography (silica gel/petroleum ether:ethyl acetate=2:1)).

Workup

  1. temperaturethe mixture is refluxed for 1 hour until deproteination
  2. temperaturethe mixture is refluxed for 3 hours
  3. temperatureAfter cooling
  4. dry with materialthe organic phase is dried over MgSO4
  5. customConcentration of the solvent gives
  6. custom1.1 g (crude product which is purified by flash chromatography (silica gel/petroleum ether:ethyl acetate=2:1))

Sources & evidence

ORD record
ord-e768b8b3fc42492e8d55a14560d1b19b
Source dataset
uspto-grants-1997_01
Patent number
US05595992

Reaction notes

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