Nitric Acid → HCID 22325288, compound

HRID 496358Notes

Reaction equation

HRID 496358 reaction equation
[OH2:1].O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].[N+](=C[C:16]([CH:18]=[N+]=[N-])=[O:17])=[N-].[CH3:21][O:22][C:23]1[C:40]([O:41][CH3:42])=[C:39]([O:43][CH3:44])[C:38]([O:45][CH3:46])=[C:37]([CH3:47])[C:24]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29](CCC(O)=O)=[CH:28][CH:27]=1.[N+]([O-])(O)=O.O1CCO[CH2:54][CH2:53]1>O.[Ag]=O>[CH3:21][O:22][C:23]1[C:40]([O:41][CH3:42])=[C:39]([O:43][CH3:44])[C:38]([O:45][CH3:46])=[C:37]([CH3:47])[C:24]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:53][CH2:54][CH2:18][C:16]([OH:1])=[O:17])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 312751,4-DioxaneHCID 61475Sodium Thiosulfate PentahydrateHCID 131725150HCID 131725150, compound

Product 1

HCID 22325288HCID 22325288, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

Sodium thiosulfate pentahydrate (230 mg, 0.93 mmol) and silver oxide (130 mg, 0.56 mmol) were dissolved in water (5 ml) and the mixture was heated to 50° C. to 70° C. A solution of the compound (380 mg, 0.98 mmol) obtained in Step 1 in dioxane (3.5 ml) was added dropwise, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was cooled and was acidified with an aqueous solution of diluted nitric acid and then was extracted with ether. The extract was washed with water, dried, and then the solvent was distilled off to yield the title compound (210 mg, 0.54 mmol, yield 93%).

Workup

  1. temperaturethe mixture was heated to 50° C. to 70° C
  2. temperatureThe reaction mixture was cooled
  3. extractionwas extracted with ether
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cf682122873546b494ac6f59e93acc8b
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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