2-Methylbenzoyl chloride → HCID 21571935, compound

HRID 1606162Notes

Reaction equation

HRID 1606162 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1CC#N.[C:10]1([CH3:19])[C:11]([C:16](Cl)=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:16]([C:11]2[C:10]([CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:17])=[CH:5][CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-

Product 1

HCID 21571935HCID 21571935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

-2-acetonitrile: To a solution of 24 g. (0.20 mole) of 1-methylpyrrole-2-acetonitrile and 30.92 g. (0.20 mole) o-toluoyl chloride in 200 ml. methylene chloride (cooled externally to -20°C.) is added dropwise 23.4 ml. (0.20 mole) of stannic chloride. After the addition is complete, the yellow mixture is permitted to come to room temperature. The mixture is then poured into ice-dilute hydrochloric acid. The two phases are separated. The organic phase is washed consecutively with N,N-dimetyl-1,3-propanediamine, 3N hydrochloric acid, and saturated sodium chloride solution; dried over magnesium sulfate; and the product, 1-methyl-5-(o-toluoyl)-pyrrole-2-acetonitrile, is separated from the residual oil by chromatography. The column is packed with acid washed alumina in hexane. The eluant is benzene. The product is found in the first compoundbearing fraction as determined by ultraviolet absorption at 260 mμ. The benzene is evaporated and the resultant solid is purified by recrystallization twice from methaol, m.p. 90°-92.5°C.

Workup

  1. additionis added dropwise 23.4 ml
  2. additionAfter the addition
  3. customto come to room temperature
  4. additionThe mixture is then poured into ice-dilute hydrochloric acid
  5. customThe two phases are separated
  6. washThe organic phase is washed consecutively with N,N-dimetyl-1,3-propanediamine, 3N hydrochloric acid, and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customand the product, 1-methyl-5-(o-toluoyl)-pyrrole-2-acetonitrile, is separated from the residual oil by chromatography
  9. washwashed alumina in hexane
  10. customas determined by ultraviolet absorption at 260 mμ
  11. customThe benzene is evaporated
  12. customthe resultant solid is purified by recrystallization twice from methaol, m.p. 90°-92.5°C.

Sources & evidence

ORD record
ord-9b94f29afc7e43deb04c4124fccb707d
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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