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

HRID 1636798Notes

Reaction equation

HRID 1636798 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-61206834f14b4020a88600726b9685f6
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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