Water → 6-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1516109

Reaction equation

HRID 1516109 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[N+:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2Cl)([O-:18])=[O:17].O>O1CCCC1>[N+:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2[O:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79410p-tert-Butylphenethyl alcoholHCID 113562574-Chloro-6-nitroquinazoline

Product 1

HCID 596786596-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-tert-butylphenyl)ethanol (1.0 g, 5.59 mmol) is dissolved in dry tetrahydrofuran (7 ml) and to it is added sodium hydride (48.5 mg, 2.02 mmol). The resulting solution is stirred at room temperature for 30 minutes after which 6-Nitro-4-chloroquinazoline (1.17 g, 5.6 mmol) is added to the above solution. The solution is then stirred for 6 hours after which water is added to the mixture. The solution is then extracted in dichloromethane. The organic layer is washed, dried and then concentrated to yield the crude product which is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to give the product.

Workup

  1. additionis added to the above solution
  2. additionis added to the mixture
  3. extractionThe solution is then extracted in dichloromethane
  4. washThe organic layer is washed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66994f89b43541d8bfc3f1bb7cef1177
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Linked notes

Loading…