Potassium Carbonate → HCID 86690962, compound

HRID 1055655Notes

Reaction equation

HRID 1055655 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].[CH3:14][N:15]([CH3:21])[CH2:16][CH2:17][CH2:18][NH:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:14][N:15]([CH3:21])[CH2:16][CH2:17][CH2:18][N:19]([CH3:20])[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 5190373-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 86690962HCID 86690962, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

500 mg (2.64 mmol) of 3-fluoro-5-(trifluoromethyl)benzonitrile, 338 mg (2.91 mmol) of N,N,N′-trimethylpropane-1,3-diamine and 767 mg (5.52 mmol) of potassium carbonate in 5.0 ml of DMSO were stirred at 110° C. for 8 h. The reaction mixture was then separated directly into its components by preparative HPLC (Method 12). The product fractions were freed from the solvent, the residue was suspended in ethyl acetate and the suspension was washed successively with saturated aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate and concentrated. This gave 290 mg (38% of theory) of the title compound.

Workup

  1. customThe reaction mixture was then separated directly into its components by preparative HPLC (Method 12)
  2. washthe suspension was washed successively with saturated aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b5861f84e46b48aaac4c2702ec919f88
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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