Hydrochloric Acid → HCID 178432900, compound

HRID 1930553Notes

Reaction equation

HRID 1930553 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[N:14]#[C:15][NH2:16].Cl>C(O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:15]([NH2:16])=[NH:14])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9864CyanamideHCID 31574784-(2-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 178432900HCID 178432900, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-methyl-1H-imidazol-1-yl)aniline (2 g, 11.55 mmol) in ethanol (25 mL) was added cyanamide (0.728 g, 17.32 mmol) and hydrochloric acid (1.422 mL, 17.32 mmol). The reaction mixture was refluxed for 4 h. An additional 1 eq of hydrochloric acid (1.422 ml, 17.32 mmol) was added and precipitation occurred. The precipitated product was filtered off and washed with DCM to give 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (1.600 g, 64.4%). MS (ESI+)/(ESI−) m/z 216/214

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customprecipitation
  3. filtrationThe precipitated product was filtered off
  4. washwashed with DCM

Sources & evidence

ORD record
ord-1c0fa56ff9f44c43a91ffde3562bedc2
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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