Hydrochloric Acid → 2-Chloro-5-(5-Chloro-2-Thienyl)Pyrrole-3-Carbonitrile

HRID 374525Notes

Reaction equation

HRID 374525 reaction equation
Cl.[Cl:2][C:3]1[S:7][C:6]([C:8]([CH2:10][CH:11]([C:14]#[N:15])[C:12]#[N:13])=O)=[CH:5][CH:4]=1.CCOCC.C(Cl)(Cl)[Cl:22]>CCCCCC.CCOCC>[Cl:22][C:12]1[NH:13][C:8]([C:6]2[S:7][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:10][C:11]=1[C:14]#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6212ChloroformHCID 15296965[(5-Chloro-2-Thenoyl)Methyl]Malononitrile

Product 1

HCID 152969642-Chloro-5-(5-Chloro-2-Thienyl)Pyrrole-3-Carbonitrile

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

Hydrogen chloride gas is bubbled through a mixture of [(5-chloro-2-thenoyl)methyl]malononitrile (4.60 g, 20.5 mmol), ether and chloroform at a moderate rate for 20 minutes. The reaction mixture is poured into an ice-water mixture and extracted with ether. The combined organic extracts are dried over MgSO4 and concentrated in vacuo to give a brown solid. The solid is mixed with a hexane/ether solution and filtered to obtain the title product as a brown solid, mp >200° C.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a brown solid
  5. filtrationfiltered

Sources & evidence

ORD record
ord-300cab6eda344d8c81bc1303eca396fa
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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