Triethylamine → 4-chloro-N-methoxy-N-methylbutyramide

HRID 1778570Notes

Reaction equation

HRID 1778570 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([N:3]([O:4][CH3:5])[CH3:2])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 112522004-chloro-N-methoxy-N-methylbutyramideYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While under argon, a solution of N,O-dimethylhydroxylamine hydrochloride (16.9 g, 0.173 mol) and triethylamine (53 mL, 0.381 mol) in dichloromethane (240 mL) was carefully treated with 4-chlorobutyryl chloride (20 g, 0.19 mol) over 40 minutes. After the addition was complete, the reaction mixture was stirred overnight at room temperature. The solid triethylamine hydrochloride was removed by filtration and the remaining solution was washed successively with aq 2 N HCl (×2), 1M K2CO3 and saturated aqueous sodium chloride. The organic layer was dried over MgSO4, filtered and concentrated to give 4-chloro-N-methoxy-N-methylbutanamide (21.8 g) of crude yellow oil that was used in the next step without further purification. ESI MS found for C6H12ClNO2 m/z [166.0/168.0 (M+1)].

Workup

  1. additionAfter the addition
  2. customThe solid triethylamine hydrochloride was removed by filtration
  3. washthe remaining solution was washed successively with aq 2 N HCl (×2), 1M K2CO3 and saturated aqueous sodium chloride
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16b22acfd96e4925b117371c096a0200
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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