Ethylamine → 3-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

HRID 1387187Notes

Reaction equation

HRID 1387187 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1.C(N)C.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[C:13]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:8]2[CH:9]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[N:6]=[CH:7]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 6456Trityl chlorideHCID 178520509HCID 178520509, compound

Product 1

HCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.0 g (15.85 mmol) of 4-(3-hydroxypropyl)-1H-imidazole and 5.5 ml (54.3 mmol) of dry ethylamine in 15.6 ml of dimethylformamide is treated with 4.86 g (17.4 mmol) of triphenylmethyl chloride in 5 ml of dimethylformamide under nitrogen. The mixture obtained is stirred at room temperature for 2 hours and is then poured onto 350 g of crushed ice. The resulting solid is collected by filtration, washed three times with water and purified on a chromatographic column using, as eluent, chloroform and then a chloroform/methanol (1/1) mixture to give 1-triphenylmethyl-4-(3-hydroxypropyl)-1H-imidazole, M.p.: 132°-133° C.

Workup

  1. customThe mixture obtained
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed three times with water
  4. custompurified on a chromatographic column

Sources & evidence

ORD record
ord-ae44abd74ecb4346855c20853232ab99
Source dataset
uspto-grants-2001_07
Patent number
USRE037303E1

Reaction notes

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