Toluene → N-Methoxy-N-methylbutyramide

HRID 2183625Notes

Reaction equation

HRID 2183625 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][NH:9][O:10][CH3:11].C1(C)C=CC=CC=1.[C:19](Cl)(=[O:23])[CH2:20][CH2:21][CH3:22]>O>[CH3:11][O:10][N:9]([CH3:8])[C:19](=[O:23])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8855Butyryl chlorideHCID 11430Potassium CarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 13704543N-Methoxy-N-methylbutyramide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (62.4 g) was added in portions at 0° C. over 10 minutes to a stirred solution of N,O-dimethylhydroxylamine hydrochloride (250 g) in water (250 ml), then toluene (250 ml) was added and the mixture was stirred until the internal temperature reached 2° C. Butyryl chloride (26 ml) was added dropwise over 10 minutes, then the mixture was stirred at 0° C. for 5 minutes and at ambient temperature for 1 hour. The aqueous phase was separated and shaken with toluene (2×100 ml), then the combined toluene solutions were dried (Na2SO4) and the solvent was removed in vacuo to give N-methoxy-N-methylbutyramide (21.0 g) as a pale-yellow oil which was used without further purification.

Workup

  1. customreached 2° C
  2. stirringthe mixture was stirred at 0° C. for 5 minutes and at ambient temperature for 1 hour
  3. customThe aqueous phase was separated
  4. stirringshaken with toluene (2×100 ml)
  5. dry with materialthe combined toluene solutions were dried (Na2SO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-20fd7ff7995041dfa6a74d59b7bb6d4d
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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