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

HRID 2370925Notes

Reaction equation

HRID 2370925 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:4]=[CH:3]1.[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:11][O:10][C:8](=[O:9])[CH2:7][C:5]1[N:4]=[CH:3][N:2]([C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178499561HCID 178499561, compound

Product 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl esterYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.78 g (19.80 mmol) of the compound from example 1c, 5.52 g (19.80 mmol) of triphenylmethyl chloride and 2.00 g (19.80 mmol) of triethylamine in 5 ml of DMF was stirred at RT overnight, then poured into 200 ml of water and stirred at RT for one hour. The precipitate which separated out was filtered off with suction. The filtrate was extracted three times with EA. The combined organic phases were dried over Na2SO4, filtered and concentrated. The yellow oil resulting from this and the precipitate were combined and chromatographed on silica gel. 4.2 g of the desired compound resulted.

Workup

  1. customThe precipitate which separated out
  2. filtrationwas filtered off with suction
  3. extractionThe filtrate was extracted three times with EA
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe yellow oil resulting from this and the precipitate
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-d0fe411866234d048d329ce677358396
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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