Sodium Hydroxide → N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamide

HRID 1432415Notes

Reaction equation

HRID 1432415 reaction equation
[OH-:1].[Na+].[CH2:3](Cl)[C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1.Cl.[CH3:15][NH:16][O:17][CH3:18]>O.C(#N)C>[CH3:18][O:17][N:16]([CH3:15])[C:3]([C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1)=[O:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 10921728N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium hydroxide (12.0 g, 300 mmol) in water (15 mL) was added slowly to a solution of piperonyl chloride (5.55 g, 30 mmol) and N,O-dimethylhydroxylamine hydrochloride (3.53 g, 36 mmol) in acetonitrile (200 mL). The mixture was stirred at room temperature for 0.5 h. Acetonitrile was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Column chromatography on silica gel eluting with ethyl acetate:hexanes (30:70) gave 5.5 g (88%) of the title compound as a yellow oil. MS (ES+) m/z 210.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 1H), 7.26 (d, 1H, J=1.3 Hz), 6.86 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 3.61 (s, 3H), 3.38 (s, 3H).

Workup

  1. customAcetonitrile was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ff03ca517ba4dd9aa52720f661e9f6a
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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