Water → HCID 14054586, compound

HRID 1381986Notes

Reaction equation

HRID 1381986 reaction equation
[NH2:1][CH:2]([CH:5]([CH3:7])[CH3:6])[C:3]#[N:4].C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19](Cl)=[O:20].O>C(Cl)Cl.C(OCC)(=O)C>[C:3]([CH:2]([NH:1][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][N:24]=[C:16]([Cl:15])[CH:17]=1)[CH:5]([CH3:7])[CH3:6])#[N:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 104191372-Amino-3-methylbutyronitrile

Product 1

HCID 14054586HCID 14054586, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g (0.02 mol) of 2-amino-3-methylbutyronitrile and 2.8 ml (0.02 mol) of triethylamine were dissolved in 30 ml of methylene chloride. The solution was cooled to 10° C. or below and 3.0 g (0.017 mol) of 2-chloroisonicotinoyl chloride was added dropwise thereto at 10° C. or below lest unfavorable heat generation should occur. Then, the mixture was stirred at room temperature for 1.5 h to conduct a reaction. Water and ethyl acetate were added thereto to conduct extraction. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain an oil, which was purified according to silica gel column chromatography to obtain 3.4 g (yield: 84.1%) of the intended product in the form of a colorless oil.

Workup

  1. temperatureThe solution was cooled to 10° C. or below
  2. customat 10° C. or below
  3. customa reaction
  4. extractionextraction
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto obtain an oil, which
  9. customwas purified

Sources & evidence

ORD record
ord-28ed7540e052408fb994dbfb08c66436
Source dataset
uspto-grants-1989_02
Patent number
US04804762

Reaction notes

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