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

HRID 1199102Notes

Reaction equation

HRID 1199102 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]2[S:19][C:12]3=[N:13][C:14]([OH:18])=[CH:15][C:16](=[O:17])[N:11]3[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[CH:1]1([CH2:7][CH2:8][C:9]2[S:19][C:12]3=[N:13][C:14]([OH:18])=[C:15]([N+:20]([O-:22])=[O:21])[C:16](=[O:17])[N:11]3[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1355181302-(2-cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 1354573272-(2-cyclohexylethyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 125 ml of acetic acid was suspended 9.77 g of 2-(2-cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one, and 3.5 ml of fuming nitric acid was added thereto dropwise while stirring under ice-cooling. The stirring was continued at room temperature for an additional 2.5 hours, and the precipitate formed was collected by filtration and washed successively with water, isopropanol, and diethyl ether to obtain 10.3 g of 2-(2-cyclohexylethyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as a pale yellow crystal.

Workup

  1. additionwas added
  2. temperaturecooling
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed successively with water, isopropanol, and diethyl ether

Sources & evidence

ORD record
ord-c504b092d7614c408813d14e628886b9
Source dataset
uspto-grants-1990_02
Patent number
US04898943

Reaction notes

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