Pyridine → HCID 68481761, compound

HRID 2239903Notes

Reaction equation

HRID 2239903 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]([CH2:14][C:15](Cl)=[O:16])#[N:13].N1C=CC=CC=1>ClCCCl>[C:12]([CH2:14][C:15]([NH:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:16])#[N:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 110515942-Cyanoacetyl chlorideHCID 58332105ethyl 1-amino-1H-imidazole-2-carboxylate

Product 1

HCID 68481761HCID 68481761, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 100 ml RB flask was added ethyl 1-amino-1H-imidazole-2-carboxylate (0.4 g, 2.58 mmol) from (1a), DCE (12.0 mL), 2-cyanoacetyl chloride (0.320 g, 3.09 mmol) and pyridine (0.417 mL, 5.16 mmol). The resulting mixture was stirred overnight under nitrogen at room temperature. The reaction was concentrated and diluted with ethyl acetate and washed with water (2×), then the aqueous was back-extracted with ethyl acetate. The organics were collected, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide ethyl 1-(2-cyanoacetamido)-1H-imidazole-2-carboxylate (0.38 g, 66.3% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water (2×)
  4. extractionthe aqueous was back-extracted with ethyl acetate
  5. customThe organics were collected
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c8af879c25a42d9b33a458ae5da62e7
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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