Hydrochloric Acid → 1-Methyl-5-(5-methyl-2-thenoyl)-pyrrole-2-acetonitrile

HRID 1606163Notes

Reaction equation

HRID 1606163 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[S:10][C:9]([C:11](Cl)=[O:12])=[CH:8][CH:7]=1.[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][C:21]#[N:22].Cl>ClCCCl>[CH3:14][N:15]1[C:19]([C:11](=[O:12])[C:9]2[S:10][C:6]([CH3:5])=[CH:7][CH:8]=2)=[CH:18][CH:17]=[C:16]1[CH2:20][C:21]#[N:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 215458671-Methyl-5-(5-methyl-2-thenoyl)-pyrrole-2-acetonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 25.54 g. (0.019 mole) anhydrous aluminum chloride in 70 ml. of 1,2-dichloroethane is added 30.7 g. (0.019 mole) 5-methyl-2-thenoyl chloride. The resulting solution is added dropwise to a chilled (0°C.) solution of 24 g. (0.02 mole) 1-methylpyrrole-2-acetonitrile. After the addition, the solution is stirred at room temperature for approximately 40 minutes and than heated at reflux for 3 minutes and poured onto ice acidified with dilute hydrochloric acid. The two phases are separated. The organic phase is washed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution. It is then dried over magnesium sulfate and the solvent evaporated. The resulting solid, 1-methyl-5-(5-methyl-2-thenoyl)-pyrrole-2-acetonitrile, is separated by filtration and purified by washing in cold methanol and benzene, m.p. 118°-121°C.

Workup

  1. additionTo a suspension of 25.54 g
  2. additionThe resulting solution is added dropwise to
  3. additionAfter the addition
  4. temperaturethan heated
  5. temperatureat reflux for 3 minutes
  6. additionpoured onto ice
  7. customThe two phases are separated
  8. washThe organic phase is washed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution
  9. dry with materialIt is then dried over magnesium sulfate
  10. customthe solvent evaporated
  11. customThe resulting solid, 1-methyl-5-(5-methyl-2-thenoyl)-pyrrole-2-acetonitrile, is separated by filtration
  12. custompurified
  13. washby washing in cold methanol

Sources & evidence

ORD record
ord-a8a2e0d058cb4523aa6894b2f1d8afa6
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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