Sodium Chloride → HCID 53985058, compound

HRID 1007242Notes

Reaction equation

HRID 1007242 reaction equation
[F:1][CH:2]([F:27])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13](=[O:18])[C:14]([O:16]C)=O)=[C:5]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:4]=1[C:23]([O:25][CH3:26])=[O:24].[OH-].[NH4+:29].[Na+].[Cl-]>C(Cl)Cl>[F:1][CH:2]([F:27])[C:3]1[N:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[C:6]([C:13](=[O:18])[C:14]([NH2:29])=[O:16])=[C:5]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:4]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 54504625HCID 54504625, compound

Product 1

HCID 53985058HCID 53985058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 16.5 g of methyl 6-(difluoromethyl)-4-(2-methylpropyl)-5-(methoxycarbonyl)-2-(trifluoromethyl)-a-oxo-3-pyridineacetate (prepared by example E of U.S. Pat. No. 5,298,479) in 60 ml of methylene chloride was added 25 ml of concentrated ammonium hydroxide. The reaction mixture was stirred for 2 h and the aqueous layer was saturated with NaCl and the organic was extracted into methylene chloride. The methylene chloride layer was dried (MgSO4) and concentrated in vacuo. The residue was recrystallized from 20% EtOAc-benzene to give 12.5 g of 6-(difluoromethyl) -4-(2-methylpropyl)-5-(methoxy-carbonyl)-2-(trifluoromethyl)-a-oxo-3-pyridineacetamide. A mixture of 2.4 g of this material, 2.0 g of phosphorus pentasulfide, 2 g of Celite and 16 ml of toluene was held at reflux for 2h. The mixture was filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (20% EtOAc in hexane) to give an oil which crystallized from 3% EtOAc in hexane as a solid.

Workup

  1. extractionthe organic was extracted into methylene chloride
  2. dry with materialThe methylene chloride layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from 20% EtOAc-benzene

Sources & evidence

ORD record
ord-0291d641bfba432082098b1dc1096ed3
Source dataset
uspto-grants-2004_09
Patent number
US06794396B2

Reaction notes

Loading…