Trityl chloride → (5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

HRID 621190Notes

Reaction equation

HRID 621190 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:22][C:23]1[N:24]=[CH:25][NH:26][C:27]=1[CH2:28][OH:29].C(N(CC)CC)C>CN(C=O)C>[CH3:22][C:23]1[N:24]([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[N:26][C:27]=1[CH2:28][OH:29]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178433279HCID 178433279, compound

Product 1

HCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanolYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triphenylchloromethane (13.1 g) in dry DMF (80 ml) was added dropwise over 30 min. to a stirred solution of 4-methyl-5-imidazolemethanol hydrochloride (7.0 g) and triethylamine (9.52 g) in dry DMF (75 ml) at room temperature under nitrogen, and stirring was continued for 2.5 h. The suspension was poured onto ice (600 ml), stirred for 30 min. and filtered. The resulting solid (12.0 g) was triturated twice with acetone (2×250 ml) to give the title compound (8.4 g), t.l.c. (System A 94.5:5:0.5) Rf 0.19.

Workup

  1. additionThe suspension was poured onto ice (600 ml)
  2. stirringstirred for 30 min.
  3. filtrationfiltered
  4. customThe resulting solid (12.0 g) was triturated twice with acetone (2×250 ml)

Sources & evidence

ORD record
ord-7d1fdc4436914575bd7b4787d2bda8dd
Source dataset
uspto-grants-1989_04
Patent number
US04822881

Reaction notes

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