Hydrochloric Acid → HCID 12902852, compound

HRID 128086Notes

Reaction equation

HRID 128086 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1.Cl.[N:24]1C=CC=C[CH:25]=1>>[C:25]([C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1)#[N:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12902851HCID 12902851, compound

Product 1

HCID 12902852HCID 12902852, compound

Procedure

A mixture of 64 g. (0.18 mole) of the product of step B, 17.8 g. (0.2 mole) of cuprous cyanide and 35 ml. of pyridine is heated under a nitrogen atmosphere at 150° to 160° C. for one day. The mixture is poured into 1 liter of 3 N hydrochloric acid, extracted with 1 liter of dichloromethane, and the extracts are dried. Evaporation provides a residue which is chromatographed on silica gel, eluting with dichloromethane, to provide 7-cyano-3,5-diphenylbenzofuran as a pale yellow solid. The structural assignment is supported by infrared and nuclear magnetic resonance spectral analysis.

Workup

  1. additionA mixture of 64 g
  2. extractionextracted with 1 liter of dichloromethane
  3. customthe extracts are dried
  4. customEvaporation
  5. customprovides a residue which
  6. customis chromatographed on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-385b4936c58745779f96e0b3b962cc5d
Source dataset
uspto-grants-1981_03
Patent number
US04258213

Reaction notes

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