Trichloroacetonitrile → 3-amino-4,4,4-trichloro-2-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)but-2-enamide

HRID 1850693Notes

Reaction equation

HRID 1850693 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5])#[N:2].C([O-])(=O)C.[Na+].[Cl:24][C:25]([Cl:29])([Cl:28])[C:26]#[N:27]>C(O)C>[NH2:27][C:26]([C:25]([Cl:29])([Cl:28])[Cl:24])=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]1[N:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 11011Trichloroacetonitrile2×HCID 517045Sodium Acetate2×HCID 904117632-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)acetamide

Product 1

HCID 1317324523-amino-4,4,4-trichloro-2-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)but-2-enamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)acetamide (100 mg, 0.4162 mmol) in Ethanol (1.5 mL) was sequentially added sodium acetate (68.28 mg, 0.8324 mmol), 2,2,2-trichloroacetonitrile (0.051 mL, 0.5016 mmol) and the reaction was stirred at room temperature for 4 h. A further 10 mg of sodium acetate and 10 uL 2,2,2-trichloroacetonitrile was sequentially added and the mixture was stirred for a further 2 h at RT. The reaction was concentrated in vacuo and the residue was partitioned between water and EtOAc. Combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give 3-amino-4,4,4-trichloro-2-cyano-N-(2-methyl-1-phenyl-1H-imidazol-5-yl)but-2-enamide as a redish oil. (153 mg, 79%). MS (ES+) 384.0.

Workup

  1. stirringthe mixture was stirred for a further 2 h at RT
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionCombined organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af3f1adaec8847dbb4522a2ea583c986
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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