Nitric Acid → 2-(4-tert-butylphenyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1906527Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

10.0 g of 2-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one was suspended in 100 ml of acetic acid, and 15 ml of fuming nitric acid was added dropwise to the suspension while maintaining the temperature at 80° C. After completion of the reaction, the mixture was cooled and the precipitate was separated by filtration to obtain 7.1 g of 2-(4-tert-butylphenyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as pale yellow prisms having a melting point of 245° to 246° C. (decomposition).

Workup

customAfter completion of the reaction
temperaturethe mixture was cooled
customthe precipitate was separated by filtration

Sources & evidence

ORD record: ord-444adab23cf44b609ae1c80e44e5d8f5
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04652646

Reaction notes

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