Acetone → HCID 21043795, compound

HRID 2043324Notes

Reaction equation

HRID 2043324 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:13][C:14]([CH3:16])=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Cl:12][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH:14]([CH3:16])[CH3:13])=[CH:7][C:6]=1[C:8]([F:9])([F:10])[F:11]

Participants

6

Reactant 3

HCID 180AcetoneHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21043795HCID 21043795, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

5-Amino-2-chlorobenzotrifluoride (0.587 g, 3.0 mmol) was dissolved in methanol (30 ml). Then acetone (1.58 ml, 30 mmol) and zinc chloride (1.635 g, 12 mmol) were added and the reaction mixture was cooled with an ice bath. After adding sodium cyanoborohydride (0.566 g, 9.0 mmol) the mixture was allowed to stir at 40° C. overnight. After cooling, the reaction mixture was poured onto ammonium chloride/ice and extracted with ethyl acetate (2 times 50 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=95:5) to yield a light yellow oil (0.530 g, 74%) that was directly used for the next step; MS (EI): 222.1 ((M-CH3)+); 237.1 (M+.).

Workup

  1. temperaturethe reaction mixture was cooled with an ice bath
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ammonium chloride/ice
  4. extractionextracted with ethyl acetate (2 times 50 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-97c7001edf2945aa9d1cc3d794721e39
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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