Phosphorus oxychloride → HCID 89375780, compound

HRID 1752258Notes

Reaction equation

HRID 1752258 reaction equation
[O:1]1[C:6]2[CH:7]=[N:8][NH:9][C:10](=O)[C:5]=2[CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:10]1[N:9]=[N:8][CH:7]=[C:6]2[O:1][CH2:2][CH2:3][CH2:4][C:5]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89375802HCID 89375802, compound

Product 1

HCID 89375780HCID 89375780, compoundYield 59.5%

Procedure

3,4-Dihydro-2H-pyrano[2,3-d]pyridazin-5(6H)-one (400 mg, 2.63 mmol) was stirred in phosphorus oxychloride (4 mL, 6.58 g, 42.9 mmol) at 95° C. for nearly 2 hours. The reaction was then cooled to room temperature and excess phosphorus oxychloride was removed in vacuo. The residue was treated with ice (˜15 g) and very slowly with solid potassium carbonate until pH >7. A tan solid was isolated by filtration and dried under vacuum to afford the title compound (267 mg, 57% yield). MS (ESI) [m/e, (M)+]=170.6. 1H NMR (400 MHz, chloroform-d) δ ppm 8.68 (s, 1H), 4.28-4.42 (m, 2H), 2.78 (t, J=6.32 Hz, 2H), 2.05-2.20 (m, 2H).

Workup

  1. customexcess phosphorus oxychloride was removed in vacuo
  2. additionThe residue was treated with ice (˜15 g) and very slowly with solid potassium carbonate until pH >7
  3. customA tan solid was isolated by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cb51f369e9664e0e9889cad08725e557
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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