Thionyl Chloride → HCID 53411291, compound

HRID 848501Notes

Reaction equation

HRID 848501 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(Cl)([Cl:17])=O>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([Cl:17])=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 53411291HCID 53411291, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 50 g. of 3-(3-nitrophenyl)propenoic acid, 24.54 ml. of thionyl chloride and 300 ml. of benzene were heated under reflux for 2.5 hours. The cooled solution was filtered and then it was evaporated in vacuo. The residue was recrystallized from carbon tetrachloride, to give 49.9 g. (91% yield) of the title compound, m.p. 81°-83.5° C.

Workup

  1. additionA mixture of 50 g
  2. temperatureunder reflux for 2.5 hours
  3. filtrationThe cooled solution was filtered
  4. customit was evaporated in vacuo
  5. customThe residue was recrystallized from carbon tetrachloride
  6. customto give 49.9 g

Sources & evidence

ORD record
ord-4bc709618a3446d399e48fd5ecd351b6
Source dataset
uspto-grants-1981_10
Patent number
US04296120

Reaction notes

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