Thionyl Chloride → N-Chloromethyl-3-(2-chlorophenyl)-4-cyanopyrrole

HRID 1285299Notes

Reaction equation

HRID 1285299 reaction equation
O[CH2:2][N:3]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4]1.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][CH2:2][N:3]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202487964-(2-Chlorophenyl)-1-(hydroxymethyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 20248789N-Chloromethyl-3-(2-chlorophenyl)-4-cyanopyrrole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With efficient stirring, 48 g of N-hydroxymethyl-3-(2-chlorophenyl)-4-cyanopyrrole are added in several portions to 60 ml of thionyl chloride such that moderate gas evolution is maintained. When the evolution of gas ceases, the mixture is stirred for 2 hours at room temperature and then for 21/2 hours at 35°-40° C. After cooling to room temperature, toluene is added and the mixture is concentrated. The residue is recrystallised from diethyl ether/petroleum, affording the title compound in the form of beige crystals with a melting point of 97°-99° C.

Workup

  1. temperatureis maintained
  2. custom2 hours
  3. customat 35°-40° C
  4. temperatureAfter cooling to room temperature
  5. concentrationthe mixture is concentrated
  6. customThe residue is recrystallised from diethyl ether/petroleum

Sources & evidence

ORD record
ord-720854440be648f3b55d36630bcdc097
Source dataset
uspto-grants-1986_01
Patent number
US04567052

Reaction notes

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