Benzyltrimethylammonium hydroxide → HCID 70546733, compound

HRID 2057375Notes

Reaction equation

HRID 2057375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([C:13]1[NH:14][CH2:15][CH2:16][N:17]=1)[CH2:10][C:11]#[CH:12].[OH-].C[N+](C)(C)CC1C=CC=CC=1>C(O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:13]2=[N:14][CH2:15][CH2:16][N:17]2[C:11]([CH3:12])=[CH:10]1

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 20332207N-(2,6-Dichlorophenyl)-N-(prop-2-yn-1-yl)-4,5-dihydro-1H-imidazol-2-amine

Product 1

HCID 70546733HCID 70546733, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 702EthanolCatalyst

Procedure

A mixture consisting of 5.4 gm of 2-[N-(2,6-dichloro-phenyl)-N-propargyl-amino]-2-imidazoline and 40 ml of ethanol containing 5 drops of trimethylbenzyl ammonium hydroxide was refluxed for five hours, while stirring. Thereafter, the ethanol was evaporated in vacuo, and the residue was dissolved in dilute hydrochloric acid. The resulting solution was fractionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide). The thin-layer chromatographically uniform ethereal fractions having a pH of 9 or more were combined, dried over magnesium sulfate, and the ether was evaporated in vacuo, leaving 1 gm (18.7% of theory) of 7-(2,6-dichloro-phenyl)-2,3-dihydro-5-methyl-imidazo[1,2-α]imidazole, m.p. 113°-117° C.

Workup

  1. temperaturewas refluxed for five hours
  2. customThereafter, the ethanol was evaporated in vacuo
  3. dissolutionthe residue was dissolved in dilute hydrochloric acid
  4. extractionThe resulting solution was fractionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide)
  5. dry with materialdried over magnesium sulfate
  6. customthe ether was evaporated in vacuo

Sources & evidence

ORD record
ord-03058b514d05496faa348475546a3566
Source dataset
uspto-grants-1980_07
Patent number
US04210659

Reaction notes

Loading…