Benzyltrimethylammonium hydroxide → HCID 19429541, compound

HRID 1078393Notes

Reaction equation

HRID 1078393 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6]C(=C)C(N)=O)=[CH:4][CH:3]=1.[Cl:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1[Cl:20].[OH-:21].[CH2:22]([N+:29](C)(C)C)[C:23]1C=CC=C[CH:24]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:29][C:22](=[O:21])[CH2:23][CH2:24][N:16]2[C:15]([Cl:14])=[C:19]([Cl:20])[N:18]=[CH:17]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 1400184,5-DichloroimidazoleHCID 86749734HCID 86749734, compound

Product 1

HCID 19429541HCID 19429541, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N-[-(4-chlorobenzyl)acrylamide (Example V) (3.9 g), 4,5-dichloroimidazole (2.7 g), benzyltrimethylammonium hydroxide (Triton B) (0.20 ml of 40% solution in methanol) and pyridine (13 ml) was boiled under reflux for 8 hours. The mixture was evaporated down under reduced pressure and the residue dissolved in dichloro-methane (100 ml). This solution was washed with water (3×100 ml) and then extracted with 5M hydrochloric acid (3×50 ml). The combined acid extracts were basified with 5M sodium hydroxide and the product extracted into dichloromethane to give a yellow oil which was triturated with hot petroleum ether (b.p. 60°-80° C.) to give solid N-(4-chlorobenzyl)-3-(4,5-dichloroimidazol-1-yl)propionamide which was sufficiently pure by 1H nmr spectroscopy for use in part (b) below.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe mixture was evaporated down under reduced pressure
  3. dissolutionthe residue dissolved in dichloro-methane (100 ml)
  4. washThis solution was washed with water (3×100 ml)
  5. extractionextracted with 5M hydrochloric acid (3×50 ml)
  6. extractionthe product extracted into dichloromethane
  7. customto give a yellow oil which
  8. customwas triturated with hot petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-c5a90a1cd68241908816e9f906daded3
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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