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

HRID 1054429Notes

Reaction equation

HRID 1054429 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. MS (ESI): m/z 166.1 (M+H).

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-96646fcc76424fb68b0ac11870a646e7
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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