Thiophenol → 2-Amino-3-cyano-5-formyl-4-phenylthiothiophene

HRID 1591298Notes

Reaction equation

HRID 1591298 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:10]=[O:11])=[C:5](Cl)[C:6]=1[C:7]#[N:8].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[O-].[Na+]>CO>[NH2:1][C:2]1[S:3][C:4]([CH:10]=[O:11])=[C:5]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 197667672-Amino-3-cyano-5-formyl-4-phenylthiothiopheneYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18.7 parts of 2-amino-4-chloro-3-cyano-5-formylthiophene are added to a solution of 11 parts of thiophenol, 5.4 parts of a 30% strength methanolic sodium methylate solution and 100 parts of methanol. The mixture is heated at the boil for 0.5 hour, after which it is allowed to cool and the precipitated product is filtered off under suction, washed with methanol, and then with water and dried. 21 parts (81% of theory) of 2-amino-3-cyano-5-formyl-4-phenylthiothiophene are obtained.

Workup

  1. temperatureThe mixture is heated at the boil for 0.5 hour
  2. temperatureto cool
  3. filtrationthe precipitated product is filtered off under suction
  4. washwashed with methanol
  5. dry with materialwith water and dried

Sources & evidence

ORD record
ord-70ddab2daf19419bbaa22ed55c413ed2
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

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