Water → HCID 12115477, compound

HRID 2373328Notes

Reaction equation

HRID 2373328 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][CH:8]([C:13]1[CH:19]=[C:18]([C:20](F)([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:14]=1[NH2:15])[CH2:9][CH:10]([CH3:12])[CH3:11].O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:7][CH:8]([C:13]1[CH:19]=[C:18]([CH:20]([C:21]([F:22])([F:23])[F:24])[C:25]([F:27])([F:28])[F:26])[CH:17]=[CH:16][C:14]=1[NH2:15])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 22734601HCID 22734601, compound

Product 1

HCID 12115477HCID 12115477, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum lithium hydride (2 g, 52.7 mmol) was suspended in tetrahydrofuran (60 ml), followed by adding dropwise thereto 2-(1,3-dimethylbutyl)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (14 g, 40.5 mmol), and the resulting mixture was stirred at reflux temperature for 3 hours. Water was added to the reaction mixture in small portions under ice-cooling, followed by stirring for 10 minutes. Magnesium sulfate was added thereto and then stirred for 10 minutes. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to obtain 13 g of the desired compound.

Workup

  1. additionby adding dropwise
  2. temperatureat reflux temperature for 3 hours
  3. temperaturecooling
  4. stirringstirred for 10 minutes
  5. filtrationThe reaction mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d948fc099af47f392b2d1d997b3c77a
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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