Trimethylsilyl cyanide → 3,3,3-Trifluoro-2-(4-methoxybenzylamino)-2-methyl propanenitrile

HRID 444944Notes

Reaction equation

HRID 444944 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]=[C:11]([CH3:16])[C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=1.[C:17]([Si](C)(C)C)#[N:18].[Br-].[Mg+2].[Br-].[C:26]([O-:29])(O)=O.[Na+]>C(Cl)Cl>[F:13][C:12]([F:15])([F:14])[C:11]([NH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:29][CH3:26])=[CH:4][CH:5]=1)([CH3:16])[C:17]#[N:18]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 82241Magnesium BromideHCID 516892Sodium BicarbonateHCID 866576701-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

Product 1

HCID 866576713,3,3-Trifluoro-2-(4-methoxybenzylamino)-2-methyl propanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine (4.41 g, 19.07 mmol) in DCM (100 ml) was added cyanotrimethylsilane (2.84 g, 28.6 mmol) and magnesium bromide. The mixture was stirred at RT for 90 h and then diluted with sat. NaHCO3 (200 ml). After stirring at RT for 1 h, the organic phase was separated, washed with a further portion of sat. NaHCO3 (100 ml), dried over MgSO4 and concentrated in vacuo to afford the title compound.

Workup

  1. stirringAfter stirring at RT for 1 h
  2. customthe organic phase was separated
  3. washwashed with a further portion of sat. NaHCO3 (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93043912563d44eb97ae1cff70cfdf88
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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