m-Chloroperbenzoic acid → 4-Amino-2-methylsulfinyl-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

HRID 727215Notes

Reaction equation

HRID 727215 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([S:19][CH3:20])[N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([S:19]([CH3:20])=[O:26])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 197052704-Amino-2-methylthio-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

Product 1

HCID 197052624-Amino-2-methylsulfinyl-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

A stirred solution of 1.5 grams (0.005 mole) of 4-amino-2-methylthio-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline (prepared as in Example 16) in 20 mL of chloroform is cooled to -10° C., and a solution of 1.7 grams (0.005 mole) of 50-60% 3-chloroperoxybenzoic acid in 30 mL of chloroform is added dropwise at a rate to maintain the reaction mixture temperature at -10° C. Upon completion of addition, the reaction mixture is maintained at -10° C. for one hour. After this time the reaction mixture is allowed to warm to ambient temperature, where it stands for about 18 hours. The reaction mixture is then washed with an aqueous 10% solution of potassium carbonate. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel, yielding 4-amino-2-methylsulfinyl-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture is maintained at -10° C. for one hour
  3. temperatureto warm to ambient temperature
  4. washThe reaction mixture is then washed with an aqueous 10% solution of potassium carbonate
  5. dry with materialThe organic layer is dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure to a residue

Sources & evidence

ORD record
ord-4d09e3c6161c487e84fb9af30423867d
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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