Aminoacetonitrile → HCID 17961245, compound

HRID 901824Notes

Reaction equation

HRID 901824 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:15][CH2:16][C:17]#[N:18]>O1CCOCC1.Cl>[C:16]([CH2:17][NH:18][S:9]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:2]([F:14])([F:13])[F:1])(=[O:11])=[O:10])#[N:15]

Participants

5

Reactant 2

HCID 10901AminoacetonitrileHCID 179612474-(trifluoroMethyl)pyridine-3-sulfonyl chloride

Product 1

HCID 17961245HCID 17961245, compoundYield 28.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-Trifluoromethyl-pyridine-3-sulfonyl chloride (0.45 g) was dissolved in dioxane (3 ml), and ami-noacetonitrile (1.0 g) was added to the mixture and allowed to stand at ambient temperature overnight. The reaction was diluted with 0.5% HCl and 37% HCl was added dropwise until the mixture became acidic. This was extracted three times with ethyl acetate. The ethyl acetate portions were combined, washed with saturated sodium bicarbonate and dried with magnesium sulfate. The drying agent was filtered away and the solvent evaporated to give 0.14 g of crude 4-Tri-fluoromethyl-pyridine-3-sulfonic acid cyanomethyl-amide, which was chromatographed an silica gel using methylene chloride to yield 0.06 g of purified 4-Trifluoromethyl-pyridine-3-sulfonic acid cyanomethyl-amide. LC/ms analysis with RT=1.12 min yielded a purity of 99% m+/m− of 265.87/263.88. Melting point of the purified compound tested as 158-159° C.

Workup

  1. additionwas added dropwise until the mixture
  2. extractionThis was extracted three times with ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. filtrationThe drying agent was filtered away
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-de7afa0286a045efbe787c4f4604d9d7
Source dataset
uspto-grants-2008_04
Patent number
US07365042B2

Reaction notes

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