Iodoethanol → HCID 20255117, compound

HRID 638052Notes

Reaction equation

HRID 638052 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)=[CH:11][CH:10]=1.OCCI>CN(C)C=O>[OH:4][CH2:2][CH2:1][N:16]1[CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[N:19]=[C:15]1[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 12225IodoethanolHCID 23665647Potassium tert-butoxideHCID 178488961HCID 178488961, compound

Product 1

HCID 20255117HCID 20255117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At an internal temperature of 0°-50°, 35.0 g of potassium tert.-butoxide are added to a solution of 35 g of 2-(4-methoxyphenyl)-4-(trifluoromethyl)-imidazole in 200 ml of dimethylformamide. After 20 minutes, a solution of 14.7 ml of 2-hydroxyethyl iodide in 100 ml of dimethylformamide is added dropwise within a period of 5 minutes, the mixture is then stirred for 120 hours at room temperature and the solvent is removed in a rotary evaporator; the residue is taken up in water and extracted several times with ethyl acetate. The organic phases are combined, the solvent is removed and the residue is chromatographed on silica gel with the solvent mixture ethyl acetate/hexane 1:1 and 1-(2-hydroxyethyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole is isolated from the main fractions in the form of a crystallising oil.

Workup

  1. customthe solvent is removed in a rotary evaporator
  2. extractionextracted several times with ethyl acetate
  3. customthe solvent is removed
  4. customthe residue is chromatographed on silica gel with the solvent mixture ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-3ff00a070ee74eb5ae397ef180e0b181
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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