Hydrochloric Acid → HCID 53411291, compound

HRID 380722Notes

Reaction equation

HRID 380722 reaction equation
[N+](C1C=C([O:10][C:11](=O)[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)C=CC=1)([O-])=O.[N+](C1C=C(C=CC=1)C=CC(O)=O)([O-])=O.S(Cl)([Cl:40])=O.Cl>CN(C=O)C.C(OCC)(=O)C>[N+:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH:13]=[CH:12][C:11]([Cl:40])=[O:10])([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-HCID 78569128HCID 78569128, compound

Product 1

HCID 53411291HCID 53411291, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Synthesis of (3′-nitrophenyl)-3-nitrocinnamate 193.2 g (1 mole) of 3-nitrocinnamic acid and 650 g of ethyl acetate were placed in a reaction vessel. While 200 g of thionyl chloride with some drops of DMF was dropped into the reaction mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and poured into hexane. The precipitate was separated by filtration and dried. 205 g of 3-nitrocinnamoyl chloride was yielded.

Workup

  1. customwere placed in a reaction vessel
  2. customthe reaction mixtures
  3. temperaturewere refluxed
  4. concentrationThe reacted solution was concentrated until a solid
  5. customcould be precipitated
  6. additionpoured into hexane
  7. customThe precipitate was separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-026af577c6fd4b86bca30de19a404e48
Source dataset
uspto-grants-2001_10
Patent number
US06303742B1

Reaction notes

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