Nitromethane → 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1085618Notes

Reaction equation

HRID 1085618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=O)O[C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[CH:4][CH:3]=1.ClC(=C)[C:20]#[N:21].[N+]([CH3:26])([O-])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:26][C:12]=2[C:20]#[N:21])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 701982-ChloroacrylonitrileHCID 157530294-(p-Chlorophenyl)2-trifluoromethyl-2-oxazolin-5-one

Product 1

HCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Conditions

Temperature
-5 °C

Procedure

4-(p-chlorophenyl)-2-(trifluoromethyl)-2-oxazolin-5-one (2.5 g; 0.01 mol) is dissolved in nitromethane (50 mL). In a single portion, 2-chloroacrylonitrile (8.0 mL; 0.01 mol) is added to the solution, and the resulting solution is stirred 18 hours at reflux under a nitrogen atmosphere. Cooling the red/brown solution to -5° C. in an ice-acetone bath causes the formation of a precipitate which is collected by filtration and washed with a small portion of cold nitromethane. The resulting tan solid is recrystallized from hot ethylene dichloride yielding the product as white crystals (1.8 g; 56% theory), m.p. 238°-241° C. (dec.).

Workup

  1. temperatureat reflux under a nitrogen atmosphere
  2. filtrationis collected by filtration
  3. washwashed with a small portion of cold nitromethane
  4. customThe resulting tan solid is recrystallized from hot ethylene dichloride yielding the product as white crystals (1.8 g; 56% theory), m.p. 238°-241° C. (dec.)

Sources & evidence

ORD record
ord-15600fe1868e426db4eb59fff75d1999
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Reaction notes

Loading…