Phosphorus oxychloride → HCID 66839224, compound

HRID 546756Notes

Reaction equation

HRID 546756 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([NH2:13])=O)[CH:6]=[CH:5][C:4]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1.P(Cl)(Cl)(Cl)=O>>[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]#[N:13])[CH:6]=[CH:5][C:4]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66839442(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide

Product 1

HCID 66839224HCID 66839224, compoundYield 68.9%

Conditions

Temperature
90 °C

Procedure

A mixture of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide (3.54 g) and phosphorus oxychloride (12 ml) was stirred at 90° C. for one hour. The reaction solution was concentrated under reduced pressure and then diluted with ice water, chloroform and aqueous ammonia, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was diluted with ether and the precipitated crystals were collected by filtration. The crystals were washed with ether and then air-dried to obtain 2.27 g of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ice water, chloroform and aqueous ammonia
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with ether
  7. filtrationthe precipitated crystals were collected by filtration
  8. washThe crystals were washed with ether
  9. customair-dried

Sources & evidence

ORD record
ord-34b11d30932d42f0a57346c0496b0ad3
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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