Hydrochloric Acid → HCID 20330198, compound

HRID 2071783Notes

Reaction equation

HRID 2071783 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

Conditions

Temperature
220 °C

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 1 day. The reaction mixture is 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 1 of benzene and the mixture is stirred for 1 hour. The mixture is then filtered. The filtrate is washed with 6N hydrochloric acid, water, 10% 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. temperaturemaintained at this temperature for 1 day
  2. stirringThe mixture is stirred
  3. temperaturewith heating below its boiling point for 1 hour
  4. customThe aqueous portion is removed
  5. additionthe organic portion is mixed with 1.2 1 of benzene
  6. stirringthe mixture is stirred for 1 hour
  7. filtrationThe mixture is then filtered
  8. washThe filtrate is washed with 6N hydrochloric acid, water, 10% sodium hydroxide solution and saturated sodium chloride solution
  9. dry with materialthen dried over magnesium sulfate
  10. customThe benzene solution is then evaporated
  11. customto provide a dark oil which

Sources & evidence

ORD record
ord-3b5ab15e01704d3cad8ab3e43ffab254
Source dataset
uspto-grants-1977_09
Patent number
US04048323

Reaction notes

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