Phosphorus oxide (P4O10) → HCID 178430871, compound

HRID 1488117Notes

Reaction equation

HRID 1488117 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][CH2:8][C:9]([NH2:11])=O)[NH:5][CH:6]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][CH2:8][C:9]#[N:11])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 178430872HCID 178430872, compound2×

Product 1

HCID 178430871HCID 178430871, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Into a 250-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, were placed a solution of 3-(4-methyl-1H-imidazol-2-yl)propanamide (compound 232.3, 2 g, 13.06 mmol) in toluene (100 mL) and P2O5 (2 g, 14.08 mmol). The reaction mixture was stirred for 12 h at 120° C., then quenched with 100 mL of water. The aqueous phase was extracted with 2×200 mL of ethyl acetate and the combined organic layers were washed with 2×100 mL of sodium carbonate (sat.), dried over sodium sulfate and concentrated under reduced pressure. This resulted in 1 g (57%) of 3-(4-methyl-1H-imidazol-2-yl)propanenitrile as light yellow oil

Workup

  1. customInto a 250-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customquenched with 100 mL of water
  4. extractionThe aqueous phase was extracted with 2×200 mL of ethyl acetate
  5. washthe combined organic layers were washed with 2×100 mL of sodium carbonate (sat.)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThis resulted in 1 g (57%) of 3-(4-methyl-1H-imidazol-2-yl)propanenitrile as light yellow oil

Sources & evidence

ORD record
ord-98bc76a8d6854e46b9b8e959ce76572f
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…