Sulfuric Acid → HCID 57468505, compound

HRID 656487Notes

Reaction equation

HRID 656487 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:24]=C(O)C=[CH:27][CH:28]=1.S(=O)(=O)(O)O.P(Cl)(Cl)(Cl)=O>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:19]3[C:18](=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=3)[O:17][C:15](=[O:16])[CH:14]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 90073-MethoxyphenolHCID 24813Phosphorus oxychlorideHCID 57468506HCID 57468506, compound

Product 1

HCID 57468505HCID 57468505, compound

Procedure

A mixture of 1 mmol of ethyl 3-(1-benzyl-1H-imidazol-4-yl)-3-oxopropionate and 1 mmol of 3-methoxyphenol [150-19-6] is admixed dropwise at 0° C. with 0.5 ml of concentrated sulphuric acid. 0.25 ml of phosphoryl chloride is added and the reaction mixture is stirred at room temperature for 17 hours. It is poured into a 1:1 mixture of ice and saturated, aqueous sodium hydrogen carbonate solution and extracted with chloroform (3×). The combined organic phases are dried over sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. additionIt is poured into a 1:1 mixture of ice
  2. extractionsaturated, aqueous sodium hydrogen carbonate solution and extracted with chloroform (3×)
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-2b43c36874784ccf913c956357e30876
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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