Sulfuric Acid → HCID 54536771, compound

HRID 728822Notes

Reaction equation

HRID 728822 reaction equation
[CH3:1][C:2](=[CH2:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1.S(=O)(=O)(O)O.[OH-:22].[Na+].[C:24](#[N:26])[CH3:25]>C(O)(=O)C.O>[N:11]1([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([NH:26][C:24](=[O:22])[CH3:25])([CH3:1])[CH3:16])=[CH:10][CH:9]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 54173499HCID 54173499, compound

Product 1

HCID 54536771HCID 54536771, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 27 g (0.126 mol) of 1-[4-(2-methyl-2-propenyloxy)phenyl]-1H-imidazole in a solution of 78 mL of glacial acetic acid and 29 mL of acetonitrile. Cool this solution to 0° C. over an ice bath and add 29.0 mL of 95% sulfuric acid dropwise at a rate to keep temperature below 15° C. Upon completionof the addition, stir overnight at room temperature. After this time, make basic (pH=12-14) with 4 N sodium hydroxide. Dilute with 400 mL of water and extract with 3×400 mL of diethyl ether. Concentrate the combinedether extracts to 350 mL on the rotary evaporator and cool in the refrigerator for 1 h. Filter off the resulting precipitate to provide the title compound.

Workup

  1. customtemperature below 15° C
  2. additionthe addition
  3. extractionextract with 3×400 mL of diethyl ether
  4. concentrationConcentrate the combinedether extracts to 350 mL
  5. customon the rotary evaporator
  6. temperaturecool in the refrigerator for 1 h
  7. filtrationFilter off the resulting precipitate

Sources & evidence

ORD record
ord-9443ea7371f249b6987ca0e4ad93f695
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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