Triethylamine → HCID 19879853, compound

HRID 1885748Notes

Reaction equation

HRID 1885748 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][N:5]=[C:6](Cl)[C:7]([F:10])([F:9])[F:8].Cl[C:17](=[CH2:20])[C:18]#[N:19].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCCC>CN(C)C=O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]1[NH:5][C:6]([C:7]([F:10])([F:9])[F:8])=[CH:20][C:17]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 19879855HCID 19879855, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 19879853HCID 19879853, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(o-chlorobenzyl)-2,2,2-trifluoroacetimidoyl chloride (10.0 g, 0.039 mol) and 2-chloroacrylonitrile (4.1 g, 0.047 mol) in N,N-dimethylformamide is cooled to 5° C. and treated with a solution of triethylamine (12.0 mL, 0.086 mol) in N,N-dimethylformamide (10 mL). When the addition is one-quarter complete, the cooling bath is removed and the reaction mixture is treated with the remaining triethylamine solution, stirred for three hours, diluted with water and extracted with methylene chloride. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an oil. Flash chromatography of the oil using silica gel and a 1:6 ethyl acetate/heptane solution gives an oil. Crystallization of the oil from heptane gives the title product as a solid (8.5 g, mp 151°-152.5° C.).

Workup

  1. additionWhen the addition
  2. customthe cooling bath is removed
  3. additionthe reaction mixture is treated with the remaining triethylamine solution
  4. additiondiluted with water
  5. extractionextracted with methylene chloride
  6. washThe combined organic extracts are washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto obtain an oil
  10. customCrystallization of the oil from heptane

Sources & evidence

ORD record
ord-4cd3a58b378242429dc470fee8d5285a
Source dataset
uspto-grants-1992_09
Patent number
US05145986

Reaction notes

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