2-Methylbenzoyl chloride → HCID 18424146, compound

HRID 1275286Notes

Reaction equation

HRID 1275286 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9].[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]=[C:3]1[CH2:7][C:8]#[N:9]

Participants

4

Reactant 2

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

Product 1

HCID 18424146HCID 18424146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-dimethyl-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 compound bearing fraction as determined by ultraviolet absorption at 260 mμ. The benzene is evaporated and the resultant solid is purified by recrystallization twice from methanol, 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-dimethyl-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 methanol, m.p. 90-92.5° C.

Sources & evidence

ORD record
ord-3a046e9725c04abfba5fd26d7495640a
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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