Phosphorus oxychloride → HCID 18446569, compound

HRID 1268841Notes

Reaction equation

HRID 1268841 reaction equation
[I:1][C:2]1[S:10][C:9]2[C:8]([C:11]#[N:12])=[CH:7][NH:6][C:5](=O)[C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:5]1[C:4]2[CH:3]=[C:2]([I:1])[S:10][C:9]=2[C:8]([C:11]#[N:12])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 184465252-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 18446569HCID 18446569, compound

Procedure

To 2-iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile 25 (7.75 g, 25.6 mmol) was added POCl3 (90 mL). The reaction was stirred under reflux overnight. POCl3 was removed by rotary evaporation followed by suspension of solids in H2O (500 mL) and filtration. The solids were washed with copious amounts of H2O, saturated bicarbonate solution, and washed further with H2O to provide upon drying 7.52 g of 26. 1H NMR (400 MHz, d6-DMSO) δ 8.82 (s, 1H), 8.06 (s, 1H).

Workup

  1. temperatureunder reflux overnight
  2. customPOCl3 was removed by rotary evaporation
  3. additionfollowed by suspension of solids in H2O (500 mL)
  4. filtrationfiltration
  5. washThe solids were washed with copious amounts of H2O, saturated bicarbonate solution
  6. washwashed further with H2O
  7. customto provide
  8. dry with materialupon drying 7.52 g of 26

Sources & evidence

ORD record
ord-d48673329def480ab4236aed695bed3e
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

Loading…