Trityl chloride → 4-Methyl-1-trityl-1H-imidazole

HRID 2107760Notes

Reaction equation

HRID 2107760 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1>C1(C)C=CC=CC=1>[CH3:28][C:29]1[N:30]=[CH:31][N:32]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418800HCID 178418800, compound

Product 1

HCID 6182544-Methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of trityl chloride (17 g), triethylamine (8.5 ml), 4-methylimidazole (5 g) and toluene (40 ml) was stirred at 80° for 4 h and filtered, and the solid material was washed with toluene. It was then partitioned between water and chloroform, and the chloroform solution was separated, dried and combined with the dried toluene filtrate. The combined organic solutions were evaporated to dryness under reduced pressure, and the residue was triturated with diethyl ether to give 4-methyl-1-tritylimidazole, mp. 214°-216°.

Workup

  1. filtrationfiltered
  2. washthe solid material was washed with toluene
  3. customIt was then partitioned between water and chloroform
  4. customthe chloroform solution was separated
  5. customdried
  6. customThe combined organic solutions were evaporated to dryness under reduced pressure
  7. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-ce547ca4e3494a80ac413573c4bf90e1
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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