Water → HCID 22628516, compound

HRID 278481Notes

Reaction equation

HRID 278481 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=1)(=O)[NH2:2].O=P(Cl)(Cl)Cl.O>CN(C=O)C>[C:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 22628493HCID 22628493, compound

Product 1

HCID 22628516HCID 22628516, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 2-(4-carbamoyl-1-imidazolyl)-4-phenyl-butyrate (obtained in Preparation 2) in DMF (5 ml) was added to an ice-cooled solution of POCl3 (0.71 ml) in DMF (6 ml) under nitrogen atmosphere. After 1.5 h, the solvent was poured into water (50 ml) and the solution was neutralized with saturated NaHCO3aq. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel (16 g) column chromatography eluting with chloroform/methanol (100:1) to give ethyl 2-(4-cyano-1-imidazolyl)-4-phenylbutyrate (435 mg, 101.2%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel (16 g) column chromatography
  6. washeluting with chloroform/methanol (100:1)

Sources & evidence

ORD record
ord-92bc8eae1cd94ac0906370619e34636f
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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