Methanol → N-(2H-1,3-Benzodioxol-5-yl)acetamide

HRID 1669161Notes

Reaction equation

HRID 1669161 reaction equation
[CH3:1][C:2](OC(C)=O)=[O:3].[CH2:8]1[O:17][C:16]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[O:9]1.CO>O1CCOCC1>[O:17]1[C:16]2[CH:15]=[CH:14][C:12]([NH:13][C:2](=[O:3])[CH3:1])=[CH:11][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic Anhydride2×HCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
16 °C

Procedure

Ac2O (21.4 mL, 226 mmol) was added dropwise to a stirred solution of 3,4-methylendioxyaniline (217) (25.87 g, 189 mmol) in dioxane (200 mL) at 0° C. and the mixture was stirred at 16° C. for 16 h. MeOH (10 mL) was added to decompose excess Ac2O and the solvent evaporated. The residue was dissolved in EtOAc (200 mL), dried and the solvent evaporated. The residue was filtered through a short column of silica, eluting with a gradient (50-100%) of EtOAc/pet. ether, to give acetamide 218 (29.17 g, 86%) as a white solid: mp 133-135° C. [lit (Krasso, A. & Ramuz, H., U.S. Pat. No. 4,599,347, 1986) mp (toluene) 138-139° C.]; 1H NMR δ 7.09 (d, J=1.8 Hz, 1H, H-4), 7.06 (br s, 1H, NH), 6.77 (dd, J=8.3, 1.8 Hz, 1H, H-6), 6.72 (d, J=8.3 Hz, 1H, H-7), 5.94 (s, 2H, H-2), 2.14 (s, 3H, CH3).

Workup

  1. customthe solvent evaporated
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. customdried
  4. customthe solvent evaporated
  5. filtrationThe residue was filtered through a short column of silica
  6. washeluting with a gradient (50-100%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-108368b3093946eeb142d65365743fc2
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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