2,6-Dichloroaniline → HCID 19814841, compound

HRID 465886Notes

Reaction equation

HRID 465886 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[H-].[Na+].[H][H].F[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([CH3:25])[N:16]=1>CS(C)=O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH:4][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:18]=[C:17]([CH3:25])[N:16]=1

Participants

6

Reactant 4

HCID 118462,6-DichloroanilineHCID 24758Sodium hydrideHCID 19814843133564-25-7HCID 178418361HCID 178418361, compound

Product 1

HCID 19814841HCID 19814841, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

4.0 g (0.025 mol) of 2,6-dichloroaniline in 20 ml of dimethyl sulfoxide are added dropwise at 15°-20° C. to 1.2 g (0.05 mol) of sodium hydride in 20 ml of dimethyl sulfoxide. After hydrogen has ceased to evolve, 4.5 g (0.025 mol) of 2-fluoro-4-trifluoromethyl-6-methylpyridine in 10 ml of dimethyl sulfoxide are added dropwise, whereupon the temperature rises to 30° C. The reaction mixture is stirred for 2 hours at room temperature and then ice-water is added. After extraction with diethyl ether, the ether phase is dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed over silica gel with ethyl acetate/hexane (1:3), affording 4.4 g (54.8%) of the title compound of formula ##STR28## in the form of crystals which melt at 108° C. (compound 2.033).

Workup

  1. customrises to 30° C
  2. extractionAfter extraction with diethyl ether
  3. dry with materialthe ether phase is dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed over silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-833367caa6a54dd9aab923705ea4bf1d
Source dataset
uspto-grants-1992_10
Patent number
US05154751

Reaction notes

Loading…