Hydrochloric Acid → HCID 53975820, compound

HRID 614100Notes

Reaction equation

HRID 614100 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 Pat. No. 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-74d262da39014d22ab706e47e9365b36
Source dataset
uspto-grants-1979_03
Patent number
US04143154

Reaction notes

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