Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

HRID 840454Notes

Reaction equation

HRID 840454 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[NH:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.O>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([C:9]1[NH:8][CH:12]=[CH:11][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8027PyrroleHCID 11430Potassium Carbonate

Product 1

HCID 3214872-(Trichloroacetyl)pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

45 g (247 mmol) of trichloroacetyl chloride and 100 ml of ethyl ether were introduced into a three-necked flask. A solution of 15.4 g (230 mmol) of pyrrole in 100 ml of ethyl ether was added dropwise and stirring was carried out at room temperature for one hour. A solution of 20 g of potassium carbonate in 60 ml of water was then slowly added. The organic phase was separated by settling, dried over magnesium sulfate and evaporated and the residue was triturated in hexane and filtered. 42.7 g (87%) of the expected compound, with a melting point of 78°-79° C., were recovered.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customthe residue was triturated in hexane
  5. filtrationfiltered
  6. custom42.7 g (87%) of the expected compound, with a melting point of 78°-79° C., were recovered

Sources & evidence

ORD record
ord-46b4cd2b54d14067926e9e61f0be902f
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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