HCID 73605901, compound → 2-(4-Chlorophenyl)-1H-pyrrole-3-carbonitrile

HRID 1033566Notes

Reaction equation

HRID 1033566 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:10][CH2:11][CH:12]=O)=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]2[NH:10][CH:11]=[CH:12][C:7]=2[C:8]#[N:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 73605901HCID 73605901, compound

Product 1

HCID 146232102-(4-Chlorophenyl)-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 108 mL of trifluoroacetic acid stirred at 23° C. is added 54.00 g (0.183 mol) of solid p-chloro-β-[(formylmethyl)amino]cinnamonitrile, diethyl acetal over a period of 45 minutes. This addition produced an exotherm to 38° C. and, 32 minutes into the addition, a solid started to precipitate. After stirring at room temperature for 30 minutes, the reaction mixture is vacuum filtered and the collected solid is washed first with trifluoroacetic acid, secondly with an ethyl acetate-hexane mixture, and finally with hexane. The yield is 16.83 g (45.4%) of an off-white solid, mp 165°-166° C.

Workup

  1. additionThis addition
  2. customproduced an exotherm to 38° C.
  3. addition32 minutes into the addition
  4. customto precipitate
  5. filtrationfiltered
  6. washthe collected solid is washed first with trifluoroacetic acid, secondly with an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-db0b5cf6c5a446a4bfd006f6ada49c39
Source dataset
uspto-grants-1994_05
Patent number
US05310938

Reaction notes

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