Sodium Thiosulfate → 9-Bromo-2-(4-methylphenyl)-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazoline-3,5-dione

HRID 2406202Notes

Reaction equation

HRID 2406202 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7](SC)[N:6]3[C:14](=[O:24])[N:15]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:16]=[C:5]3[C:4]=2[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:33])[N:6]3[C:14](=[O:24])[N:15]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:16]=[C:5]3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 670879979-Bromo-5-(methylthio)-2-(p-tolyl)-[1,2,4]triazolo[4,3-c]quinazolin-3(2H)-one

Product 1

HCID 1358703069-Bromo-2-(4-methylphenyl)-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazoline-3,5-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7a (0.534 g, 1.33 mmol) in 60 mL of CH2Cl2 was added (77%) m-CPBA (0.597 g, 2.67 mmol) and mixture was stirred at room temperature for 6 h. A white precipitate was slowly formed. Saturated solutions of aqueous Na2S2O3 (20 mL) and NaHCO3 (20 mL) were subsequently added and the mixture was stirred vigorously for 30 min. The precipitate was filtered off, washed several times with water and heated in a mixture of 25 mL ethyl alcohol and 25 mL of water at reflux for 30 min. The mixture was cooled to rt. and filtered to give 8a as a white solid (0.488 g, 99%). mp: 369° C.;

Workup

  1. customA white precipitate was slowly formed
  2. stirringthe mixture was stirred vigorously for 30 min
  3. filtrationThe precipitate was filtered off
  4. washwashed several times with water
  5. temperatureheated in a mixture of 25 mL ethyl alcohol and 25 mL of water
  6. temperatureat reflux for 30 min
  7. temperatureThe mixture was cooled to rt
  8. filtrationand filtered

Sources & evidence

ORD record
ord-695d8e1c7cc64684af59d4739fbd5d7a
Source dataset
uspto-grants-2014_08
Patent number
US08809355B2

Reaction notes

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