Water → HCID 22379508, compound

HRID 895330Notes

Reaction equation

HRID 895330 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:16]=[CH:15][C:14]([CH3:18])([CH3:17])[CH2:13][S:12]1)([CH3:3])[CH3:2].[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[CH:23][C:24](Cl)=[N:25][CH:26]=1.[H-].[Na+].O>CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:16]([C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:29])([F:28])[F:19])=[CH:26][N:25]=2)[CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][S:12]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 223795002-(2-Isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine

Product 1

HCID 22379508HCID 22379508, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-isopropylphenyl)imino-5,5-dimethyl-1,3-thiazine (0.26 g), 5-trifluoromethyl-2-chloropyridine (0.24 g) in N,N-dimethylformamide (3 ml) was added 60% sodium hydride (0.05 g) under ice-cooling. The mixture was stirred at room temperature for 2 h. To a reaction mixture was added water (80 ml), extracted with diethylether (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2-(2-isopropylphenyl)imino-3-(5-trifluoromethyl-2-pyridyl)-5,5-dimethyl-1,3-thiazine (0.13 g, yield: 32%) as colorless oil.

Workup

  1. temperaturecooling
  2. extractionextracted with diethylether (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0adf5bff249b4b73adf83a5aad4075bb
Source dataset
uspto-grants-2005_07
Patent number
US06916806B2

Reaction notes

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