Acetyl chloride → HCID 54401905, compound

HRID 275029Notes

Reaction equation

HRID 275029 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([CH:8]=[N:9][OH:10])[CH2:3]1.C([N:13]([CH2:16][CH3:17])CC)C.[C:18](Cl)(=[O:20])[CH3:19].C(=O)(O)[O-:23].[Na+]>O.C1COCC1>[C:18]([O:20][N:13]=[C:16]([O:10][N:9]=[CH:8][C:4]1[CH2:3][N:2]([CH3:1])[CH2:7][CH2:6][CH:5]=1)[CH3:17])(=[O:23])[CH3:19]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 3072080HCID 3072080, compound

Product 1

HCID 54401905HCID 54401905, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 g (0.0142 mol) of 1-methyl-1,2,5,6-tetrahydropyridin-3-carboxaldehyde-oxime [Chem. Ber. 40, 4712, (1907) in 20 CM3 of anhydrous THF, 1.44 g (0.0142 mol) of triethylamine and 1.12 g (0.0142 mol) of acetyl chloride are added, with agitation for 1 hour at ambient temperature. The reactional mixture is treated with water, then with an aqueous solution of sodium bicarbonate; the organic phase is separated, dried and the solvent is evaporated. The residue is distilled at 0.05 mm of Hg, collecting the fraction with b.p. 170°-175°. Yield 2.1 g (81%).

Workup

  1. customthe organic phase is separated
  2. customdried
  3. customthe solvent is evaporated
  4. distillationThe residue is distilled at 0.05 mm of Hg
  5. customcollecting the fraction with b.p. 170°-175°

Sources & evidence

ORD record
ord-1a871fdc46294047bc6d4163af52edb8
Source dataset
uspto-grants-1995_02
Patent number
US05391754

Reaction notes

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