Potassium Carbonate → HCID 12811219, compound

HRID 1446959Notes

Reaction equation

HRID 1446959 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[NH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:18]=2)[CH:11]=[CH:12][CH:13]=1.[Br:23]Br.CC(C)=O.CCCCCC>O.C(Cl)(Cl)Cl>[Br:23][C:17]1[N:18]=[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=2)[NH:15][C:16]=1[C:19]([F:20])([F:21])[F:22]

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 24408Bromine2×HCID 128112112-(3-Chlorophenyl)-5-(trifluoromethyl)-1H-imidazoleHCID 21880519Acetone hexane

Product 1

HCID 12811219HCID 12811219, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Potassium carbonate is made into a paste by adding a few drops of water to 1.3 g (9.4 mol) of the potassium carbonate. The 2-(3-chlorophenyl)-5-trifluoromethylimidazole is dissolved in 100 ml chloroform and added to the flask containing the paste. 1.5 g of bromine is added and stirred. Thin layer chromatography (TLC) on alumina using 50:50 acetone-hexane clearly differentiates starting material from product. Additional bromine is added until starting material is no longer present (0.1 g). Water is added and the organic phase removed. The layer is washed with sodium bisulfite, brine and dried over sodium sulfate. The organic phase is stripped and the residue taken up in 1:1 ether hexane and filtered through silica gel, the filtrate is concentrated to yield 1.7 g product. M.P. 137°-144° C.

Workup

  1. additionadded to the flask
  2. additioncontaining the paste
  3. customthe organic phase removed
  4. washThe layer is washed with sodium bisulfite, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through silica gel
  7. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-5c32eaf141e24bec8534c683b1e29976
Source dataset
uspto-grants-1982_02
Patent number
US04314844

Reaction notes

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