Phosphorus oxychloride → HCID 18446569, compound

HRID 1868294Notes

Reaction equation

HRID 1868294 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-d3e6398932ea42cd99acbb8e56b20f26
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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