4-(Trifluoromethyl)benzoyl chloride → 1-Methyl-5-(p-trifluoromethylbenzoyl)-pyrrole-2-acetonitrile

HRID 1282354Notes

Reaction equation

HRID 1282354 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:12]([C:11]([F:10])([F:21])[F:22])=[CH:13][CH:14]=2)=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9]

Participants

4

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-

Product 1

HCID 184243881-Methyl-5-(p-trifluoromethylbenzoyl)-pyrrole-2-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.4 g. (0.12 mole) of 1-methylpyrrole-2-acetonitrile and 25 g. (0.12 mole) of p-trifluoromethylbenzoyl chloride in 120 ml. methylene chloride is chilled to −25° C. (external bath). Then 14 ml. (0.12 mole) stannic chloride is added dropwise over a half hour. The resultant suspension is permitted to come to room temperature and poured into ice-dilute hydrochloric acid. The aqueous phase is separated and washed successively with N,N-dimethyl-1,3-propane-diamine, 3N hydrochloric acid and a saturated solution of sodium chloride. The solvent is evaporated, and the product is isolated from the residual oil by column chromatography using acid-washed alumina. The solvents hexane, benzene, and ether are used as eluents. The first compound-bearing fraction not giving a positive Enrlich's test (in benzene) is collected. The solvent is evaporated and the resultant solid, 1-methyl-5-(p-trifluoromethylbenzoyl)-pyrrole-2-acetonitrile, in purified by recrystallization from isopropanol, m.p. 95-97.5° C.

Workup

  1. customto come to room temperature
  2. additionpoured into ice-dilute hydrochloric acid
  3. customThe aqueous phase is separated
  4. washwashed successively with N,N-dimethyl-1,3-propane-diamine, 3N hydrochloric acid
  5. customThe solvent is evaporated
  6. customthe product is isolated from the residual oil by column chromatography
  7. washusing acid-washed alumina
  8. customThe first compound-bearing fraction not giving a positive Enrlich's test (in benzene)
  9. customis collected
  10. customThe solvent is evaporated
  11. customthe resultant solid, 1-methyl-5-(p-trifluoromethylbenzoyl)-pyrrole-2-acetonitrile, in purified by recrystallization from isopropanol, m.p. 95-97.5° C.

Sources & evidence

ORD record
ord-5ae086ad810a405680d2d72f3531a61a
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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