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

HRID 703841Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Twenty-four (24) grams of 2-benzylthio-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was suspended in 250 ml of acetic acid and warmed to 40° C. To this suspension, 7.9 g of fuming nitric acid was added dropwise. After the addition of the nitric acid was finished, the reaction mixture was stirred at 40° C. for 5 hours. After the reaction was finished, the reaction mixture was cooled, and water was added thereto. The deposited crystals were collected by filtration, washed with water and dried under reduced pressure. Thus 24 g of 2-benzylthio-7-hydroxy-6-nitro-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 87%.

Workup

temperaturethe reaction mixture was cooled
filtrationThe deposited crystals were collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-74c5d783514941f1b7966f37330b39c7
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985432

Reaction notes

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