Phenylacetyl chloride → 2,2,2-trichloro-1-[4-(2-phenylacetyl)-1H-pyrrol-2-yl]-1-ethanone

HRID 351607Notes

Reaction equation

HRID 351607 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]([Cl:21])([Cl:20])[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[O:14].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Cl:21][C:12]([Cl:11])([Cl:20])[C:13]([C:15]1[NH:16][CH:17]=[C:18]([C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:19]=1)=[O:14]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27636082,2,2-trichloro-1-[4-(2-phenylacetyl)-1H-pyrrol-2-yl]-1-ethanoneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry flask, phenylacetyl chloride (1 equivalent) was combined with 2-trichloroacetyl pyrrole (1 equivalent) in a minimum amount of dichloromethane (DCM) to dissolve the reactants. To the resulting solution, at ambient temperature, was added aluminum trichloride (1 equivalent). After 2 hours, the reaction mixture was applied directly onto a silica gel column. Gradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield. 1H NMR (CDCl3) δ 4.0 (s, 2H), 7.1-7.35 (m, 7H), 9.7 (br s, NH). HPLC using method B provided Rt of 4.9 minutes. LC/MS (M+1) 330.2, (M−1) 328.1.

Workup

  1. dissolutionto dissolve the reactants
  2. washGradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield
  3. customprovided Rt of 4.9 minutes

Sources & evidence

ORD record
ord-a4ca777de07941e790648d8b07d7e50d
Source dataset
uspto-grants-2004_06
Patent number
US06743791B2

Reaction notes

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