Sulfuric Acid → HCID 178484896, compound

HRID 358261Notes

Reaction equation

HRID 358261 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[CH2:13](OC(OCC)OCC)C.OS(O)(=O)=O.[CH3:28][NH2:29]>C(O)C.Cl>[CH3:28][NH:29][CH:13]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6329MethylamineHCID 31214Ethyl orthoformateHCID 178507418HCID 178507418, compound

Product 1

HCID 178484896HCID 178484896, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1.59 gm of 4-(4-aminophenyl)-1-H-imidazole and 2.22 gm of triethylorthoformate was heated for 30 minutes at 100° C. in the presence of a catalytic amount of 96% H2SO4. A 33% solution of methylamine in ethanol (9.5 gm) was then added dropwise to the cooled reaction mixture. The solution was stirred at room temperature for twenty hours and then evaporated to dryness. The residue obtained was dissolved in 10% hydrochloric acid, and the acid solution was washed with ethyl acetate and then adjusted to pH 10 with 10% NaOH. The product which separated was extracted with ethyl acetate to yield, after evaporation of the solvent, 0.45 gm of the desired compound.

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. washthe acid solution was washed with ethyl acetate
  4. customThe product which separated
  5. extractionwas extracted with ethyl acetate
  6. customto yield
  7. customafter evaporation of the solvent, 0.45 gm of the desired compound

Sources & evidence

ORD record
ord-324a21efb5cb4e4c8be2b7e4d666cfff
Source dataset
uspto-grants-1984_08
Patent number
US04465841

Reaction notes

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