Carbon Dioxide → HCID 54306658, compound

HRID 261943Notes

Reaction equation

HRID 261943 reaction equation
C([Li])CCC.[CH2:6]([N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[CH:10]1)[CH:7]=[CH2:8].CN(C)CCN(C)C.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1.C(=O)=O>CCCCCC.O1CCCC1.O>[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)([C:10]2[N:9]([CH:6]=[CH:7][CH3:8])[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=2)[OH:30])=[CH:27][CH:26]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 70344,4'-DichlorobenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 21321307HCID 21321307, compoundHCID 178418339Butyllithium

Product 1

HCID 54306658HCID 54306658, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In the course of one hour, 40 ml. (0.085 mol) of a 20% butyl lithium solution in n-hexane were added dropwise with stirring, under a nitrogen atmosphere at -60° C. to a solution of 10.4 g (0.0765 mol) of 1-allyl-4,5-dimethyl-imidazole and 9.3 g (0.080 mol) of N,N,N',N'-tetramethylethylenediamine in 125 ml. of anhydrous tetrahydrofuran. Stirring was continued for another two hours at -60° C. and then 19.5 g (0.078 mol) of 4,4'-dichlorobenzophenone in 100 ml of anhydrous tetrahydrofuran were added dropwise. The reaction mixture was kept standing overnight at room temperature and then 15 ml. of water and some pieces of solid carbon dioxide were added. The mixture was filtered and the filtrate was concentrated. The residue was extracted with a mixture of diethyl ether and 2 N hydrochloric acid. The aqueous phase was made alkaline with potassium carbonate and extracted with diethyl ether. The extract was dried over sodium sulphate and concentrated. The residue was extracted again with 2 N hydrochloric acid and diethyl ether and the aqueous phase was made alkaline again with potassium carbonate. The solid matter formed was filtered off and dissolved in boiling petroleum ether (boiling range 60°-80° C.). The undissolved material was filtered off and the petroleum ether was distilled off. The residue was taken up in a very small amount of diethyl ether. The solution was cooled in a mixture of carbon dioxide and acetone and the precipitate was filtered off. α,α-Bis(p-chlorophenyl)-4,5-dimethyl-1-(1-propenyl)imidazole-2-methanol was obtained. Melting point 127°-128° C.

Workup

  1. customIn the course of one hour, 40 ml
  2. waitThe reaction mixture was kept standing overnight at room temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. extractionThe residue was extracted with a mixture of diethyl ether and 2 N hydrochloric acid
  6. extractionextracted with diethyl ether
  7. dry with materialThe extract was dried over sodium sulphate
  8. concentrationconcentrated
  9. extractionThe residue was extracted again with 2 N hydrochloric acid and diethyl ether
  10. customThe solid matter formed
  11. filtrationwas filtered off
  12. dissolutiondissolved
  13. filtrationThe undissolved material was filtered off
  14. distillationthe petroleum ether was distilled off
  15. temperatureThe solution was cooled in a mixture of carbon dioxide and acetone
  16. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-a9f6566686684bb58d6ff361e6bc1908
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

Loading…