Isopropyl iodide → HCID 20255183, compound

HRID 638051Notes

Reaction equation

HRID 638051 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[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.C(I)(C)C>CN(C)C=O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]([CH:2]([CH3:3])[CH3:1])[CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[N:19]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 23665647Potassium tert-butoxide2×HCID 178488961HCID 178488961, compound

Product 1

HCID 20255183HCID 20255183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At an internal temperature of 0°-50°, 10 g of potassium tert.-butoxide are added to a solution of 20 g of 2-(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole in 200 ml of dimethylformamide. After 20 minutes 10.7 ml of isopropyl iodide are added and the reaction mixture is subsequently stirred at room temperature. After 24 hours in each case, a further 10 g of potassium tert.-butoxide are added and then 10.7 ml of isopropyl iodide. In total, these measures are repeated three times. The total reaction period is 120 hours. Finally, the solvent is removed in a rotary evaporator, the residue is taken up in water and extracted several times with ethyl acetate. After evaporating off the organic phase, the residue is chromatographed on silica gel with ethyl acetate/hexane and 2-(4-methoxyphenyl)-1-isopropyl-4-(trifluoromethyl)-1H-imidazole is isolated from the main fractions in the form of a yellowish oil.

Workup

  1. customThe total reaction period
  2. waitis 120 hours
  3. customFinally, the solvent is removed in a rotary evaporator
  4. extractionextracted several times with ethyl acetate
  5. customAfter evaporating off the organic phase
  6. customthe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3ebd565081543c18a78102c0f691f3f
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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