Hydrochloric Acid → HCID 20330198, compound

HRID 1449338Notes

Reaction equation

HRID 1449338 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[N:17]1C=CC=C[CH:18]=1.Cl>O>[C:18]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 203301763-(4-Chlorophenyl)-1-benzofuran

Product 1

HCID 20330198HCID 20330198, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 45.2 g. (0.198 mole) of 3-(4-chlorophenyl)benzofuran, 22.2 g. (0.248 mole) of cuprous cyanide and 15 ml. of pyridine is heated to 220° C. and maintained at this temperature for one day. The mixture is then poured into a solution of 47.5 g. of ferric chloride, 30 ml. of concentrated hydrochloric acid and 135 ml. of water with stirring. The mixture is stirred with heating below its boiling point for 1 hour. The aqueous portion is removed, and the organic portion is mixed with 1.2 liter of benzene, and the mixture is stirred for 1 hour. The mixture is then filtered. The filtrate is washed with 6 N hydrochloric acid, water, 10 percent sodium hydroxide solution and saturated sodium chloride solution, then dried over magnesium sulfate. The benzene solution is then evaporated to provide a dark oil which solidifies to provide 3-(4-cyanophenyl)benzofuran. The infrared spectrum of the product is consistent with the assigned structure.

Workup

  1. additionA mixture of 45.2 g
  2. temperaturemaintained at this temperature for one day
  3. additionThe mixture is then poured into a solution of 47.5 g
  4. temperaturewith heating below its boiling point for 1 hour
  5. customThe aqueous portion is removed
  6. additionthe organic portion is mixed with 1.2 liter of benzene
  7. stirringthe mixture is stirred for 1 hour
  8. filtrationThe mixture is then filtered
  9. washThe filtrate is washed with 6 N hydrochloric acid, water, 10 percent sodium hydroxide solution and saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customThe benzene solution is then evaporated
  12. customto provide a dark oil which

Sources & evidence

ORD record
ord-a44cf22e18114821876a741f4e991de4
Source dataset
uspto-grants-1980_02
Patent number
US04190590

Reaction notes

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