Phosphorus oxychloride → 2-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

HRID 916980Notes

Reaction equation

HRID 916980 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:12]1[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 219849076-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 102371012-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

Conditions

Temperature
100 °C

Procedure

To the product of Step C of Example 129 (1.50 g, 4.40 mmol) was added POCl3 (5 mL, 53.6 mmol). The mixture was heated to 100° C. for 17 hours before concentrating in vacuo. The residue was dissolved in ethyl acetate and washed with NaHCO3 (saturated, aq.), water, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 10% ethyl acetate/hexane affording product. MS (electrospray) m/e 360.9 MH+ (Rt=4.1 min LC/MS).

Workup

  1. concentrationbefore concentrating in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with NaHCO3 (saturated, aq.), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel)
  7. washeluting with 10% ethyl acetate/hexane affording product

Sources & evidence

ORD record
ord-ec141460397d48199b8704f716a29923
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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