Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methylbenzamide

HRID 430477Notes

Reaction equation

HRID 430477 reaction equation
CN([C:4]([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl[C:24]1[CH:41]=[CH:40][C:27]([C:28]([NH:30][C:31]2C=C(C=CC=2)C(O)=O)=[O:29])=[C:26](OC)[CH:25]=1.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:4][O:8][N:30]([CH3:31])[C:28](=[O:29])[C:27]1[CH:26]=[CH:25][CH:24]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15549729HCID 15549729, compound

Product 1

HCID 569575N-Methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBTU (4.73 g, 14.7 mmol) was added to a solution of 3-{(4-chloro-2-methoxybenzoyl)amino}benzoic acid (4.50 g, 14.7 mmol), N,O-dimethylhydroxylamine hydrochloride (1.72 g, 17.7 mmol) and i-Pr2NEt (7.60 g, 58.9 mmol) in DMF (29 mL) at 25°. The reaction mixture was stirred at 25° for 2.5 h. The mixture was diluted with EtOAc (200 mL). The resulting solution was successively washed with aqueous 1 N HCl (2×75 mL), water (2×75 mL), aqueous saturated NaHCO3 (2×75 mL) and brine (75 mL), then dried (MgSO4), filtered and concentrated under reduced pressure to give the corresponding N-methoxy-N-methylbenzamide of formula 6 (4.32 g, 84% yield) as a white solid:

Workup

  1. washThe resulting solution was successively washed with aqueous 1 N HCl (2×75 mL), water (2×75 mL), aqueous saturated NaHCO3 (2×75 mL) and brine (75 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ec2a3bacb0247388b2e4e397d2977ce
Source dataset
uspto-grants-2001_11
Patent number
US06323202B1

Reaction notes

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