Water → 4‐[2‐(4‐Tert‐butylphenyl)ethoxy]‐1,2‐ dihydroquinazolin‐2‐one

HRID 1516106Notes

Reaction equation

HRID 1516106 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+].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19](=[O:27])[N:18]=1.O>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19](=[O:27])[N:18]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79410p-tert-Butylphenethyl alcoholHCID 178517800HCID 178517800, compound

Product 1

HCID 596786394‐[2‐(4‐Tert‐butylphenyl)ethoxy]‐1,2‐ dihydroquinazolin‐2‐one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-tert-butylphenyl)ethanol (0.3 g, 1.68 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 4-chloro-2-quinazolone (0.302 g, 1.68 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-6bd03d8610b847fa9250c4579d4dd1be
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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