Sodium amide → HCID 17967039, compound

HRID 1993294Notes

Reaction equation

HRID 1993294 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[NH2-].[Na+].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1)([CH2:20][CH:19]([O:22][CH2:23][CH3:24])[O:18][CH2:16][CH3:17])[C:10]#[N:11])[CH3:17]

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 75360m-Trifluoromethylphenylacetonitrile

Product 1

HCID 17967039HCID 17967039, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 30 g of 3-(trifluoromethyl)-phenylacetonitrile and 14.4 g of sodium amide in 400 ml of toluene is left with stirring at AT for 5 minutes, 66 ml of bromoacetaldehyde diethyl acetal are added and then the mixture is heated at 60° C. for 3 hours. It is concentrated under vacuum, the residue is taken up with water and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel H, eluting with a DCM/AcOEt (100/5; v/v) mixture. This gives 26 g of the expected product.

Workup

  1. waitis left
  2. concentrationIt is concentrated under vacuum
  3. extractionextracted with ether
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated under vacuum
  6. customThe residue is chromatographed on silica gel H
  7. washeluting with a DCM/AcOEt (100/5; v/v) mixture

Sources & evidence

ORD record
ord-cccee1a1224d413899d3fba765db734d
Source dataset
uspto-grants-2010_01
Patent number
US07652011B2

Reaction notes

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