Hydrochloric Acid → HCID 21332176, compound

HRID 1390951Notes

Reaction equation

HRID 1390951 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:4]=2[S:5][C:6]=1[C:7]#[N:8].Cl>C(O)(=O)C>[NH2:13][C:10]1[CH:11]=[CH:12][C:3]2[C:2]([Cl:1])=[C:6]([C:7]#[N:8])[S:5][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21332180HCID 21332180, compound

Product 1

HCID 21332176HCID 21332176, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred suspension of 0.1 mole of the nitrile in a mixture of 200 ml. of concentrated hydrochloric acid and 200 ml. of glacial acetic acid containing 72.0 g. of stannous chloride was heated to a temperature of 90° C. At this temperature heating was stopped and the reaction mixture was allowed to cool to room temperature. The product which separated was dissolved in 5% hydrochloric acid solution and filtered to remove any insoluble material. The filtrate was made basic with concentrated ammonium hydroxide solution and the precipitated solid was taken up in methylene chloride. After drying over potassium carbonate, the methylene chloride was removed in vacuo to give a solid residue. Recrystallization of this residue from nitromethane gave 6-amino-3-chlorobenzo-[b]thiophene-2-carbonitrile, m.p. 158°-160° C.

Workup

  1. additionin a mixture of 200 ml
  2. temperatureAt this temperature heating
  3. customThe product which separated
  4. dissolutionwas dissolved in 5% hydrochloric acid solution
  5. filtrationfiltered
  6. customto remove any insoluble material
  7. dry with materialAfter drying over potassium carbonate
  8. customthe methylene chloride was removed in vacuo
  9. customto give a solid residue
  10. customRecrystallization of this residue from nitromethane

Sources & evidence

ORD record
ord-7e9205c3d9074dd5b3ae29c1e24d3547
Source dataset
uspto-grants-1979_02
Patent number
US04140785

Reaction notes

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