Sodium hydride → HCID 21284128, compound

HRID 2232003Notes

Reaction equation

HRID 2232003 reaction equation
[CH2:1]([O:5][C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[C:7]=1[NH2:8])[CH2:2][CH2:3][CH3:4].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=O.C1(C)C=CC(S([CH2:31][N+:32]#[C-:33])(=O)=O)=CC=1.[H-].[Na+]>C1(C)C=CC=CC=1.C(COC)OC.O>[CH2:1]([O:5][C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[C:7]=1[N:8]1[C:16]([C:15]([O:19][CH2:20][CH3:21])=[O:18])=[CH:33][N:32]=[CH:31]1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 70211Ethyl oxoacetateHCID 161915Tosylmethyl isocyanideHCID 13052248HCID 13052248, compound

Product 1

HCID 21284128HCID 21284128, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

13.5 g (0.07 mol) of 2-butoxy-6-ethylaniline are heated on a water separator with 11.8 g (0.099 mol) of ethyl glyoxylate in 100 ml of toluene until water formation is complete. The mixture is evaporated, the residue is dried in a high vacuum and taken up in 30 ml of dimethoxyethane, and the solution is added dropwise with 13.4 g (0.069 mol) of p-toluenesulfonylmethyl isocyanide to a suspension of 4.3 g (0.14 mol) of 80% strength sodium hydride (white oil) in 20 ml of dimethoxyethane at -20° C. When the gas evolution is complete, the mixture is hydrolyzed by adding water dropwise, the reaction products are extracted with methylene chloride, and the solvent is evaporated. The residue is taken up in 50 ml of ethanol, 20 g of potassium carbonate are added, and the mixture is stirred for 2 hours at 50° C. After evaporation, the residue is taken up in toluene/water, the organic phase is dried and evaporated, and the residue is chromatographed through a silica gel column (petroleum ether/ethyl acetate 8:2). 12.1 g (55% of theory relative to aniline employed) of ethyl 1-(2-butoxy-6-ethylphenyl)imidazole-5-carboxylate, a pale yellow oil, are obtained.

Workup

  1. customThe mixture is evaporated
  2. customthe residue is dried in a high vacuum
  3. extractionthe reaction products are extracted with methylene chloride
  4. customthe solvent is evaporated
  5. addition20 g of potassium carbonate are added
  6. customAfter evaporation
  7. customthe organic phase is dried
  8. customevaporated
  9. customthe residue is chromatographed through a silica gel column (petroleum ether/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-40060d4ccdb142c4ad9856961fa8d0aa
Source dataset
uspto-grants-1988_11
Patent number
US04786312

Reaction notes

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