m-Chloroperbenzoic acid → 2-(2-n-Propoxyphenyl)-8-(1,2-Epoxy-1-Heptyl)Quinazolin-4-(3H)-One

HRID 635201Notes

Reaction equation

HRID 635201 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3].ClC1C=CC=C(C(OO)=[O:37])C=1>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14]([CH:22]3[O:37][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1361324752-(2-n-Propoxyphenyl)-8-(1-Hepten-1-yl)Quinazolin-4(3H)-One

Product 1

HCID 1355440492-(2-n-Propoxyphenyl)-8-(1,2-Epoxy-1-Heptyl)Quinazolin-4-(3H)-One

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 g (3.98 mmoles) of the compound from Example 1 is dissolved at 0° C. in 40 ml of dry chloroform. To it is added 0.98 g (3.98 mmoles) of 70% m-chloroperbenzoic acid. The mixture is allowed to come to room temperature and is stirred for 3 hours longer. It is washed 3 times with 30 ml portions of 10% sodium bisulfite solution and twice with 30 ml portions of 1 N NaOH solution, dried over MgSO4, and evaporated under vacuum. The residue (1.6 g) was chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant.

Workup

  1. customto come to room temperature
  2. washIt is washed 3 times with 30 ml portions of 10% sodium bisulfite solution
  3. dry with materialtwice with 30 ml portions of 1 N NaOH solution, dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue (1.6 g) was chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant

Sources & evidence

ORD record
ord-ee0f4533c9884a0fb97fc49e546ce8a9
Source dataset
uspto-grants-2001_02
Patent number
US06187779B1

Reaction notes

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