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

HRID 1723278Notes

Reaction equation

HRID 1723278 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-6e05778d5b684475b655ec3513c7b022
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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