Formic Acid → HCID 67216058, compound

HRID 1677559Notes

Reaction equation

HRID 1677559 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[CH:22](O)=O>ClCCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]2[CH:22]=[N:16][CH:15]=[C:11]2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 24813Phosphorus oxychlorideHCID 62291536HCID 62291536, compound

Product 1

HCID 67216058HCID 67216058, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

0.7 g (3.27 mmol) of 1-[4-(benzyloxy)pyridin-2-yl]methanamine (described in stage B) in 16 ml of formic acid is heated at reflux for 5 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 7 ml of 1,2-dichloroethane. 0.6 ml (6.54 mmol) of phosphoryl chloride dissolved in 7 ml of 1,2-dichloroethane is added. After heating at reflux for 4 hours, the reaction medium is concentrated under reduced pressure and the residue is then taken up in dichloromethane. The organic phase is washed with a saturated aqueous sodium hydrogencarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. 0.97 g of a brown oil is collected.

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. customThe residue obtained
  4. additionis added
  5. temperatureAfter heating
  6. temperatureat reflux for 4 hours
  7. concentrationthe reaction medium is concentrated under reduced pressure
  8. washThe organic phase is washed with a saturated aqueous sodium hydrogencarbonate solution
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. custom0.97 g of a brown oil is collected

Sources & evidence

ORD record
ord-0df9131919514ac0bbf9b56a91621035
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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