1,3,5-Trioxane → HCID 20569329, compound

HRID 1577759Notes

Reaction equation

HRID 1577759 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:15][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH3:14])=S)[S:9][C:5]=2[CH:4]([CH3:16])[CH2:3]1.[CH2:18]1[O:23][CH2:22]OCO1.[OH-:24].[Na+]>O>[CH3:1][C:2]1([CH3:17])[CH2:15][C:6]2[N:7]=[C:8]([N:10]3[C:11](=[O:24])[N:13]([CH3:14])[CH2:22][O:23][CH2:18]3)[S:9][C:5]=2[CH:4]([CH3:16])[CH2:3]1

Participants

5

Reactant 3

HCID 80811,3,5-TrioxaneHCID 14798Sodium HydroxideHCID 20569323HCID 20569323, compound

Product 1

HCID 20569329HCID 20569329, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Sulfuric acid, 85% concentration, (40 grams) is charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer and is cooled to about 5° C. N-(5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-N'-methylthiourea (0.015 mole) and s-trioxane (0.015 mole) are added portionwise, with stirring to the cold surfuric acid. Stirring is continued for a period of about 16 hours at room temperature. The reaction mixture is then diluted 1:1 with water and neutralized with aqueous 40% sodium hydroxide. The neutralized mixture is filtered and the filtered-off solid is washed with 3-100 ml portions of water and air dried to yield the desired product 3-(5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothizol-2-yl)-5-methyltetrahydro-1,3,5-oxidiazin-4-one.

Workup

  1. concentrationSulfuric acid, 85% concentration, (40 grams)
  2. additionis charged into a glass reaction vessel
  3. customfitted with a mechanical stirrer
  4. stirringStirring
  5. filtrationThe neutralized mixture is filtered
  6. washthe filtered-off solid is washed with 3-100 ml portions of water and air
  7. customdried

Sources & evidence

ORD record
ord-889c7fda77fc489ebdbb1147e85434b9
Source dataset
uspto-grants-1981_09
Patent number
US04289524

Reaction notes

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