Ammonium Hydroxide → (+/-)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide

HRID 984037Notes

Reaction equation

HRID 984037 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25](=[O:27])[CH3:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1.[NH4+].[OH-]>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25](=[O:27])[CH3:26])[CH:20]=[C:21]([Cl:23])[C:22]=1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 182054Acetamide, N-(3,5-dichlorophenyl)-HCID 10822766(4-Pyridyl)-(4-chlorophenyl)methanol

Product 1

HCID 22557316(+/-)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamideYield 87%

Conditions

Temperature
100 °C

Procedure

α-(4-chlorophenyl)-4-pyridinemethanol (0.0512 mol), N-(3,5-dichlorophenyl)-acetamide (0.102 mol) and polyphosphoric acid (210 g) were stirred at 140° C. for 90 minutes. The mixture was cooled to 100° C., poured out into ice water, basified with NH4OH and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was taken up in 2-propanone and diethyl ether. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The pure fraction was collected and the solvent was evaporated, yielding 17.94 g (87%) of (±)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide (interm. 28).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. filtrationThe precipitate was filtered off
  7. customthe filtrate was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1)
  9. customThe pure fraction was collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-869dee090ff949e8a3ab6fe29277a895
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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