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

HRID 1651684Notes

Reaction equation

HRID 1651684 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. The following anal. data is from a similarly prepared sample.

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-eafe58fbfa474493a67d591464a58cec
Source dataset
uspto-grants-1990_05
Patent number
US04929634

Reaction notes

Loading…