Sulfuric Acid → HCID 20569331, compound

HRID 1577756Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[CH2:20][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:12])[S:9][C:5]=2[C:4]([CH3:22])([CH3:21])[CH2:3]1.[CH2:24]1OCO[CH2:26][O:25]1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[CH3:23][C:2]1([CH3:1])[CH2:20][C:6]2[N:7]=[C:8]([N:10]3[C:11](=[O:12])[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:26][O:25][CH2:24]3)[S:9][C:5]=2[C:4]([CH3:22])([CH3:21])[CH2:3]1

Participants

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-(5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-N'-hexylurea (0.015 mole) and s-trioxane (0.015 mole) are added portionwise, with stirring to the cold sulfuric 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-(5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-5-hexyltetrahydro-1,3,5-oxadiazin-4-one.

Workup

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

Sources & evidence

ORD record: ord-0fe0a0e0446342858a4c5a82db81d963
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04289524

Reaction notes

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