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

HRID 13814Notes

Reaction equation

HRID 13814 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[C:11]([C:15]#[N:16])=[CH:10][C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 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 B (1.5 g) was added POCl3 (5 mL). The reaction was heated to 100° C. for 17 hours. After cooling to room temperature the excess POCl3 was removed in vacuo before the residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel eluted with 10% EtOAc in hexane affording the title compound. HPLC/MS: 358.9 (M+1), 360.9 (M+3); Rt=4.07 min.

Workup

  1. customwas removed in vacuo before the residue
  2. dissolutionwas dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel
  6. washeluted with 10% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-48d62cb6b197491f91d65aadea6106af
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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