Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 22938573, compound

HRID 856747Notes

Reaction equation

HRID 856747 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].O.ON1C2C=CC=C[C:25]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O.C(N(CC)CC)C>[CH3:19][O:18][N:17]([CH3:16])[O:8][C:6]([C:5]1[CH:9]=[CH:10][C:2]([CH3:25])=[CH:3][C:4]=1[C:11]([F:14])([F:13])[F:12])=[O:7]

Participants

9

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22938573HCID 22938573, compoundYield 91.2%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-fluoro-2-trifluoromethylbenzoic acid (7.00 g), N,O-dimethylhydroxylamine hydrochloride (4.26 g) and 1-hydroxybenzotriazole monohydrate (6.69 g) in DMF (100 ml) was added triethylamine (4.42 g). Then, catalytic amount of 4-(N,N-dimethylamino)pyridine was added to the mixture, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (8.38 g) was added to the mixture and the mixture was stirred for 1 day under nitrogen atmosphere. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), to give 1-[[[methoxy(methyl)amino]oxy]carbonyl]-4-methyl-2-(trifluoromethyl)benzene (8.07 g) as colorless oil.

Workup

  1. additionwas added to the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-aafacb7716ea455ab61128b5a4f6104c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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