Acetic Acid → HCID 13826894, compound

HRID 542777Notes

Reaction equation

HRID 542777 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=[O:7])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C(O)(=O)C.[N+:16]([O-])([OH:18])=[O:17]>C(OC(=O)C)(=O)C>[N+:16]([C:10]1[CH:9]=[CH:8][C:3]2[C:4]([CH:6]=[O:7])=[CH:5][S:1][C:2]=2[CH:11]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 2273281-Benzothiophene-3-carbaldehyde

Product 1

HCID 13826894HCID 13826894, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 9 g of benzo[b]thiophene-3-carboxaldehyde in 50 ml of acetic anhydride was cooled to 0° C. by means of an external ethanol/ice bath. A solution of 40 ml of acetic acid and 20 ml of fuming nitric acid was added at such a rate to maintain the temperature of the reaction at 0°-5° C. Following the addition of the reagents, the reaction mixture was stirred for 1.5 hours. The reaction mixture was poured into 500 ml of ice and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The resulting oil was treated with ethanol. A solid formed, which was recovered by filtration providing 1.3 g of 6-nitrobenzo[b]thiophene-3-carboxaldehyde, m.p. 187°-192° C.

Workup

  1. temperatureto maintain
  2. customthe temperature of the reaction at 0°-5° C
  3. additionthe addition of the reagents
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. additionThe resulting oil was treated with ethanol
  9. customA solid formed
  10. filtrationwhich was recovered by filtration

Sources & evidence

ORD record
ord-8f49e7faf8e6411eb6215971835fa8d0
Source dataset
uspto-grants-1987_04
Patent number
US04659717

Reaction notes

Loading…