Formamide → HCID 59598059, compound

HRID 1254036Notes

Reaction equation

HRID 1254036 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=O.[CH:14]([NH2:16])=O.[OH-].[Na+]>CCOC(C)=O>[CH3:1][N:2]1[CH:3]=[C:4]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[N:16]=[CH:14]1

Participants

5

Reactant 3

HCID 713FormamideHCID 14798Sodium HydroxideHCID 66986252HCID 66986252, compound

Product 1

HCID 59598059HCID 59598059, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(N-Methylglycyl)benzonitrile (2.6 g) and 20 ml of formamide were heated in a microwave tube at 210° C. for 20 min. The reaction was diluted with EtOAc, made basic with 15% aq NaOH, washed with water (3×100 mL) and brine, dried over MgSO4, filtered, and concentrated. The residue was subject to silica column chromatography (70% EtOAc in hexanes to 100% EtOAc) to give 1.05 g of 4-(1-methyl-1H-imidazol-4-yl)benzonitrile. LCMS: M+1=184.

Workup

  1. washwashed with water (3×100 mL) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2241779e2c424b86be47ae0ba4adee98
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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