Phosphorus oxychloride → HCID 178425442, compound

HRID 1860432Notes

Reaction equation

HRID 1860432 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:4]1[NH:3][CH:2]([CH3:1])[N:7]=[C:6]2[N:8]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:9]([CH3:11])=[CH:10][C:5]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136201556HCID 136201556, compound

Product 1

HCID 178425442HCID 178425442, compoundYield 84%

Procedure

A mixture of compound (5) (18.3 g, 65.0 mmol) in POCl3 (30 mL) was refluxed for 3 hours, cooled to room temperature, poured into ice water, and extracted with ethyl acetate. The combined organic extracts were washed with aqueous sodium bicarbonate, dried, and concentrated under vacuum. The residue was chromatographed (elution with 10% ethyl acetate in hexanes) to afford 16.3 g (84%) of compound (6) as a tan powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with aqueous sodium bicarbonate
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed
  7. wash(elution with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cdf95894e94b4b479eff47b54b55b788
Source dataset
uspto-grants-2003_03
Patent number
US06531475B1

Reaction notes

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