Nitric Acid → HCID 131724705, compound

HRID 1760255Notes

Reaction equation

HRID 1760255 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([O:12][C:13](=[O:15])[NH2:14])[CH2:7][C:8]([N:10]=[O:11])=[O:9].[N+:16]([O-])([OH:18])=[O:17]>C(OC(=O)C)(=O)C.C(O)(=O)C>[N+:16]([C:5]1[S:1][C:2]([CH:6]([O:12][C:13](=[O:15])[NH2:14])[CH2:7][C:8]([N:10]=[O:11])=[O:9])=[CH:3][CH:4]=1)([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 131724704HCID 131724704, compound

Product 1

HCID 131724705HCID 131724705, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

In 4 ml of acetic anhydride there was suspended (2-(2-thienyl)-2-carbamoyloxyethyl)oxocarboxamide (0.50 g) and the resulting mixture was cooled to 0°. A mixture of nitric acid (60% in water 0.37 g) in 4 ml of acetic acid was added dropwise and the mixture was stirred at room temperature for 1.5 hours, poured into 100 ml of ice water, extracted with ethyl acetate and washed with saturated brine. The extracts were dried over sodium sulfate, filtered, concentrated and purified by recrystallization from ether to yield the title compound as a yellow solid (0.07 g, yield 12%). M.p. 145-1847 (from ether).

Workup

  1. temperaturethe resulting mixture was cooled to 0°
  2. additionwas added dropwise
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialThe extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by recrystallization from ether

Sources & evidence

ORD record
ord-06552b461ccf4429ae79fdb752f5e368
Source dataset
uspto-grants-2005_01
Patent number
US06841569B2

Reaction notes

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