Pyridine → 4-chloro-N-methoxy-N-methylbutyramide

HRID 926691Notes

Reaction equation

HRID 926691 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>C(Cl)Cl>[Cl:12][CH2:13][CH2:14][CH2:15][C:16]([N:9]([O:10][CH3:11])[CH3:8])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 112522004-chloro-N-methoxy-N-methylbutyramideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (101.28 g, 106.6 mL 1281.79 mmol) was added to a solution of N,O-dimethylhydroxylamine hydrochloride (50 g, 512.72 mmol) in DCM (800 mL) at 0° C. and stirring was continued for 15 min. Chlorobutyrylchloride (72.29 g, 512.72 mmol) was then added to this mixture and was stirred continuously at 0° C. for 2 h. The reaction mixture was diluted with DCM and the organic layer was washed with water followed by brine. The organic layer was separated; dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 79 g of the title compound as a pale brown liquid.

Workup

  1. stirringwas stirred continuously at 0° C. for 2 h
  2. washthe organic layer was washed with water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b01c3186b8541ccac8cefe294740498
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

Loading…