Water → HCID 136093269, compound

HRID 843367Notes

Reaction equation

HRID 843367 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][C:14](=[NH:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].[H-].[Na+].Cl[C:26]([O:28][CH3:29])=[O:27].O>CN(C)C=O>[CH3:29][O:28][C:26](=[O:27])[NH:22][C:14](=[N:13][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:9])[F:11])=[CH:5][C:4]=1[Cl:12])[C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 178512062HCID 178512062, compound

Product 1

HCID 136093269HCID 136093269, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 0.18 g (0.50 mmol) of N-(2,6-dichloro-4-trifluoromethylphenyl)-2,2,3,3,3-pentafluoropropionamidine as present compound 4 was dissolved in 10 ml of N,N-dimethylformamide, to which 0.04 g (1.0 mmol) of sodium hydride (about 60% in oil) was added under ice cooling, and the mixture was stirred for 10 minutes. Then, 0.05 g (0.50 mmol) of methyl chloroformate was added to the reaction mixture, which was stirred at room temperature for 6 hours. Water was poured into the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.08 g of [1-(2,6-dichloro-4-trifluoromethylphenylimino)-2,2,3,3,3-pentafluoropropyl]carbamic acid methyl ester (hereinafter referred to as present compound 60).

Workup

  1. additionwas added under ice cooling
  2. stirringwas stirred at room temperature for 6 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b12abb1104df4cbfaba5d6eb44c3feac
Source dataset
uspto-grants-2002_04
Patent number
US06376710B2

Reaction notes

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