Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(4-fluorophenoxy)-N-methoxy-N-methylacetamide

HRID 2307601Notes

Reaction equation

HRID 2307601 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](Cl)=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:14][NH:15][O:16][CH3:17]>C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>[CH3:17][O:16][N:15]([CH3:14])[C:8](=[O:9])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2759057(4-Fluorophenoxy)acetyl chloride

Product 1

HCID 226078882-(4-fluorophenoxy)-N-methoxy-N-methylacetamideYield 73%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

2-(4-Fluorophenoxy)ethanoic acid chloride was added slowly to a stirred suspension of N,O-dimethylhydroxylamine hydrochloride (55.80 g, 572 mmol) in saturated K2CO3 and ethyl acetate (375 mL). A moderately exothermic reaction occurred (larger scale reactions are cooled with an ice bath), and after 20 minutes, the reaction mixture was partitioned between water and ether. The ether layer was washed with 1 M HCl and saturated NaCl, and dried over MgSO4. The dried solution was filtered and concentrated under vacuum to give N-methoxy-N-methyl-2-(4-fluorophenoxy)ethanamide, a compound of formula (Z), as a yellow oil which solidified to an off-white crystalline solid, 113.05 g (73% yield from starting acid);

Workup

  1. customA moderately exothermic reaction
  2. temperature(larger scale reactions are cooled with an ice bath)
  3. customthe reaction mixture was partitioned between water and ether
  4. washThe ether layer was washed with 1 M HCl and saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationThe dried solution was filtered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1cf4afe7e178402d84395a5aba013c5b
Source dataset
uspto-grants-2004_12
Patent number
US06831186B2

Reaction notes

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