Triethylamine → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

HRID 1459652Notes

Reaction equation

HRID 1459652 reaction equation
Br.C(C1C=CC(C[N:9]2[C:13](CC3SC=C(C4C=CC=CN=4)N=3)=[CH:12][N:11]=[CH:10]2)=CC=1)#N.C(N(CC)CC)C.[C:35]1([C:41](Br)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C[CH2:56][O:57][C:58]([CH3:60])=[O:59]>CN(C=O)C.O>[CH3:56][O:57][C:58](=[O:59])[CH2:60][C:13]1[N:9]=[CH:10][N:11]([C:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11692BromotriphenylmethaneHCID 67662460HCID 67662460, compound

Product 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step A (24.85 g, 0.141 mol) in DMF (115 mL) was added triethylamine (57.2 mL, 0.412 mol) and triphenylmethyl bromide (55.3 g, 0.171 mol) and the suspension was stirred for 24 hours. After this time, the reaction mixture was diluted with EtOAc and water. The organic phase was washed with sat. aq. NaHCO3, dried, (Na2 SO4) and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, 0-100% EtOAc in hexanes) to provide the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.35(1H,s),7.31(9H,m),7.22(6H,m), 6.76(1H,s),3.68(3H,s) and 3.60(2H,s) ppm.

Workup

  1. washThe organic phase was washed with sat. aq. NaHCO3
  2. customdried
  3. custom(Na2 SO4) and the solvent evaporated in vacuo
  4. customThe residue was purified by chromatography (Silica gel, 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b2c7dd411f244ae2a1e850beb5ba507b
Source dataset
uspto-grants-1998_12
Patent number
US05854265

Reaction notes

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