Hydrochloric Acid → HCID 178432768, compound

HRID 1382782Notes

Reaction equation

HRID 1382782 reaction equation
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])/[CH:4]=[CH:5]/[C:6]1[N:7]=[C:8]([CH3:11])[NH:9][CH:10]=1.[H][H].[ClH:16]>CO.[Pd]>[ClH:16].[CH3:13][N:2]([CH3:1])[C:3](=[O:12])[CH2:4][CH2:5][C:6]1[N:7]=[C:8]([CH3:11])[NH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178432766HCID 178432766, compound

Product 1

HCID 178432768HCID 178432768, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of (E)-N,N-dimethyl-3-(2-methyl-1H-imidazol-4-yl)-2-propenamide (340 mg) in methanol (10 ml) and HCl-saturated ethanol (2 ml) was added to a previously hydrogen-saturated suspension of 10% palladium on charcoal (50% paste with water) (35 mg) in methanol (10 ml) and the resulting suspension stirred at room temperature under hydrogen for 4 h. The mixture was filtered, concentrated in vacuo to ca. 5 ml and ethyl acetate (ca. 40 ml) was added, precipitating the title compound (275 mg) as white flakes, t.l.c. (System A 89:10:1), Rf 0.14. Addition of further ethyl acetate (40 ml) to the mother liquors precipitated further title compound (31 mg).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo to ca. 5 ml and ethyl acetate (ca. 40 ml)
  3. additionwas added
  4. customprecipitating the title compound (275 mg) as white flakes, t.l.c
  5. additionAddition of further ethyl acetate (40 ml) to the mother liquors
  6. customprecipitated further title compound (31 mg)

Sources & evidence

ORD record
ord-d7c1f4967e7b40ad91b778200c65c23f
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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