Water → HCID 19815306, compound

HRID 466433Notes

Reaction equation

HRID 466433 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[CH2:5][O:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][N:12]2[C:16]([CH2:17][OH:18])=[C:15]([Cl:19])[N:14]=[C:13]2[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)#[N:2].[CH3:30]C(C)([O-])C.[K+].CI.O>CS(C)=O>[C:1]([C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][N:12]2[C:16]([CH2:17][O:18][CH3:30])=[C:15]([Cl:19])[N:14]=[C:13]2[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:24][CH:25]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 19815336HCID 19815336, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19815306HCID 19815306, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.29 g of 1-[4-(2-cyanobenzyloxy)benzyl]-2-butyl-4-chloro-5-hydroxymethylimidazole in 8.0 mL of dimethyl sulfoxide at 25° was added 0.93 g of potassium t-butoxide followed by 0.060 mL of methyl iodide. The reaction mixture was stirred at 25° for 2.5 hours and then was poured into water. The aqueous emulsion was extracted with ethyl acetate; the organic phases were combined and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Column chromatography on silica gel (elution: 5-25% ethyl acetate/benzene) furnished 0.17 g of 1-[4-(2-cyanobenzyloxy)benzyl]-2-butyl-4-chloro-5-methoxymethylimidazole; NMR (200 MHz, CDCl3): δ 7.72-7.57 (m, 3H); 7.43 (m, 1H); 6.94 (s, 4H); 5.22 (s, 2H); 5.04 (s, 2H); 4.27 (s, 2H); 3.26 (s, 3H); 2.56 (t, 2H); 1.65 (quint., 2H); 1.33 (sext., 2H); 0.88 (t, 3H).

Workup

  1. extractionThe aqueous emulsion was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e4e6eeb552d42efb39e41cd11e6f115
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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