Hydrochloric Acid → HCID 53975820, compound

HRID 1706653Notes

Reaction equation

HRID 1706653 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[N:23]1C=CC=C[CH:24]=1.Cl>C(Cl)(Cl)Cl>[C:24]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 53901440HCID 53901440, compound

Product 1

HCID 53975820HCID 53975820, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 99 g. (0.29 mole) of the known (Belgian Patent 846,502, Example 22) compound ethyl 3-(4-bromophenyl)benzofuran-5-acetate in 40 g. of cuprous cyanide in 30 ml. of pyridine is heated at 160°-175° C. with stirring under a nitrogen atmosphere for 20 hours. To this solution is added 200 g. of ferric chloride, 100 ml. of concentrated hydrochloric acid, and 200 ml. of ice water with rapid stirring. Next, 300 ml. of chloroform is added, and the mixture is stirred for one hour, then filtered, and the insoluble material is extracted several times with chloroform. The combined chloroform extracts are dried and evaporated to provide a residue. The residue is recrystallized from a N,N-dimethyl formamide-water mixture to provide ethyl 3-(4-cyanophenyl)benzofuran-5-acetate.

Workup

  1. additionA mixture of 99 g
  2. additionTo this solution is added 200 g
  3. stirringthe mixture is stirred for one hour
  4. filtrationfiltered
  5. extractionthe insoluble material is extracted several times with chloroform
  6. dry with materialThe combined chloroform extracts are dried
  7. customevaporated
  8. customto provide a residue
  9. customThe residue is recrystallized from a N,N-dimethyl formamide-water mixture

Sources & evidence

ORD record
ord-39c702f350b644d3b1deaaac3e2e52a9
Source dataset
uspto-grants-1980_06
Patent number
US04208335

Reaction notes

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