Phosphorodichloridic acid, phenyl ester → 2-Chloro-5-(diphenylmethyl)-pyridine

HRID 1390325Notes

Reaction equation

HRID 1390325 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(OP(Cl)([Cl:30])=O)=CC=1.[OH-].[NH4+]>>[Cl:30][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 14923Ammonium HydroxideHCID 227488105-(Diphenylmethyl)-2-pyridone

Product 1

HCID 227487852-Chloro-5-(diphenylmethyl)-pyridine

Procedure

Heat 55 g. of the crude 5-(diphenylmethyl)-2-pyridone and 110 ml. of phenylphosphoric dichloride at 200°-210° with stirring for 6 hours. Pour the cooled reaction mixture onto ice, basify with ammonium hydroxide, extract with ethyl ether, dry the ether extracts, and concentrate to a residue. Distill the residue at 160°-175°/0.15 mm. and crystallize the distillate from hexane to obtain 2-chloro-5-(diphenylmethyl)-pyridine, m.p. 69.5°-71°.

Workup

  1. temperatureHeat 55 g
  2. additionPour
  3. customthe cooled reaction mixture onto ice
  4. extractionextract with ethyl ether
  5. dry with materialdry the ether
  6. concentrationconcentrate to a residue
  7. distillationDistill the residue at 160°-175°/0.15 mm
  8. customand crystallize the distillate from hexane

Sources & evidence

ORD record
ord-28aa3cb86a294f1a9214a8da89abf445
Source dataset
uspto-grants-1979_02
Patent number
US04138488

Reaction notes

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