Sulfuric Acid → HCID 13823244, compound

HRID 2231189Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH2:22][NH:21]2)[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[C:28](Cl)(=[O:31])CC.S(=O)(=O)(O)O>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH2:22][N:21]2[CH:28]=[O:31])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1 g of 2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]hexahydro-1,2,4-triazine-3,5-dione was suspended in 10 ml of formic acid. 5 ml of propionyl chloride and 1 ml of concentrated sulfuric acid were successively added dropwise, and the mixture was stirred at 80° C. for 5 hours. After it had been cooled, a further 10 ml of propionyl chloride were added to complete the reaction, and the mixture was again heated at 80° C. for 5 hours with stirring. It was then poured onto ice-water, and the precipitate was filtered off with suction and extracted by boiling with a little toluene. The residue was recrystallized from isopropanol/diisopropyl ether, melting point 212° C., decomposition.

Workup

temperatureAfter it had been cooled
customthe reaction
temperaturethe mixture was again heated at 80° C. for 5 hours
stirringwith stirring
additionIt was then poured onto ice-water
filtrationthe precipitate was filtered off with suction
extractionextracted
customThe residue was recrystallized from isopropanol/diisopropyl ether, melting point 212° C., decomposition.

Sources & evidence

ORD record: ord-82d35d1798d04180be3859456f30e867
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04782056

Reaction notes

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