Trichloromethanesulfenyl chloride → 3-Methyl-1-[(trichloromethyl)sulfanyl]quinazoline-2,4(1H,3H)-dione

HRID 1583292Notes

Reaction equation

HRID 1583292 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:13].[OH-].[K+].[Cl:16][C:17]([Cl:21])([Cl:20])[S:18]Cl>O>[Cl:16][C:17]([Cl:21])([Cl:20])[S:18][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:12])[N:2]([CH3:1])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14797Potassium HydroxideHCID 3443853-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione

Product 1

HCID 202605443-Methyl-1-[(trichloromethyl)sulfanyl]quinazoline-2,4(1H,3H)-dioneYield 35.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a suspension of 3.52 g (0.02 mole) 3-methyl-2,4-dioxo-1,3-dihydroquinazoline in 25 ml water was added a solution of 1.12 g (0.02 mole) potassium hydroxide in 15 ml water. To this clear, basic solution was added, dropwise, a mixture of 3.72 g (0.02 mole) trichloromethanesulfenyl chloride and 0.15 g of an emulsifier (as in example 1) in 2.5 ml water while maintaining the reaction mixture at 0°-5° C. The reactants were mixed so that the reaction mixture was kept at a pH greater than 7. The precipitate that formed was filtered off and the filter cake washed with water and air-dried. This was then extracted with hot benzene and the benzene removed under vacuum to yield a semi-solid oil which completely solidified on standing. The solid was recrystallized from benzene-cyclohexane to afford 2.3 g (35%) of 1-trichloromethylthio-3-methyl-2,4-dioxo-1,3-dihydroquinazoline having a melting point of 128°-129° C. Reaction of the benzene insoluble solids with additional trichloromethylsulfenyl chloride followed by the same work-up described above afforded additional product, giving an overall yield of 60%.

Workup

  1. additionTo this clear, basic solution was added
  2. temperaturewhile maintaining the reaction mixture at 0°-5° C
  3. additionThe reactants were mixed so that the reaction mixture
  4. customThe precipitate that formed
  5. filtrationwas filtered off
  6. washthe filter cake washed with water
  7. customair-dried
  8. extractionThis was then extracted with hot benzene
  9. customthe benzene removed under vacuum
  10. customto yield a semi-solid oil which
  11. customThe solid was recrystallized from benzene-cyclohexane

Sources & evidence

ORD record
ord-30fed9bf99834d31a6bcb450fec9dabe
Source dataset
uspto-grants-1985_11
Patent number
US04551458

Reaction notes

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