Nitric Acid → HCID 56763846, compound

HRID 605310Notes

Reaction equation

HRID 605310 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:7][C:8]([C:10]1[S:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:9])[CH3:6]>>[CH2:5]([O:7][C:8]([C:10]1[S:11][C:12]([Cl:15])=[C:13]([N+:1]([O-:4])=[O:2])[CH:14]=1)=[O:9])[CH3:6]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 521808Ethyl 5-chlorothiophene-2-carboxylate

Product 1

HCID 56763846HCID 56763846, compoundYield 55%

Conditions

Temperature
10 °C

Procedure

A solution of fuming nitric acid (75 mL) was cooled to 10° C. followed by the addition of 5-chloro-thiophene-2-carboxylic acid ethyl ester (15 g, 78.7 mmol). The resulting mixture was stirred for 30 minutes at 10° C. followed by the addition of ice water. The solution was then extracted with ethyl acetate and dried, then concentrated under vacuum and purified by column chromatography using silica gel to provide 10.29 g (55%) of the title product.

Workup

  1. extractionThe solution was then extracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated under vacuum
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-ab80c8d83b084772a16961669b11eb2b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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