Dimethylformamide → 3-Amino-2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine

HRID 1044840Notes

Reaction equation

HRID 1044840 reaction equation
[NH2:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]([O:8][CH:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=1.CN(C)C=O.[Cl:24]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:7]([Cl:24])=[N:6][C:5]([O:8][CH:9]([C:10]([F:11])([F:12])[F:13])[C:14]([F:17])([F:15])[F:16])=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 860624455-Amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine

Product 1

HCID 231500063-Amino-2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 5-amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine was introduced to 10 ml of N,N-dimethyl formamide, and 0.56 g of N-chlorosuccinimide was added at room temperature. The temperature was elevated to 60° C., and the mixture was stirred for 1 hour and poured into water. The mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=10:1) to give 0.50 g (yield 44%) of the title compound as a brown oil.

Workup

  1. additionwas added at room temperature
  2. customwas elevated to 60° C.
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, and thus obtained residue
  6. customwas purified by silica gel column chromatography (eluent:hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-3f7df1fc54d348c2b0eedc529d587cc3
Source dataset
uspto-grants-2013_10
Patent number
US08563736B2

Reaction notes

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