Water → HCID 15616705, compound

HRID 1381984Notes

Reaction equation

HRID 1381984 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]#[N:12].[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=1)[C:17](Cl)=[O:18].O>C(#N)C>[C:11]([CH2:10][NH:9][C:17](=[O:18])[C:16]1[CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=[C:14]([Cl:13])[CH:15]=1)#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 21275763HCID 21275763, compound

Product 1

HCID 15616705HCID 15616705, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.3 g (0.033 mol) of triethylamine was added to a solution of 1.9 g (0.02 mol) of aminoacetonitrile hydrochloride in 30 ml of acetonitrile. The mixture was stirred at room temperature for 30 min. 2.5 g (0.01 mol) of 2-chloro-6-n-butoxyisonicotinoyl chloride was added dropwise thereto under cooling at 5° to 10° C. The mixture was stirred at room temperature for 1 h, poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous common salt solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the crude product was purified according to silica gel column chromatography to obtain 1.9 g (yield: 70.9%) of white crystals having a melting point of 72° to 73° C.

Workup

  1. temperatureunder cooling at 5° to 10° C
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous common salt solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe crude product was purified

Sources & evidence

ORD record
ord-a943ad35a8194f01bab1ed25bf1bb43c
Source dataset
uspto-grants-1989_02
Patent number
US04804762

Reaction notes

Loading…