Acetic Anhydride → N-[(2H-1,3-Benzodioxol-5-yl)methyl]ethanimidic acid

HRID 1476728Notes

Reaction equation

HRID 1476728 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=2[O:2]1.[C:12](OC(=O)C)(=[O:14])[CH3:13].[OH-].[Na+]>C(O)(=O)C>[O:11]1[C:10]2[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:12](=[O:14])[CH3:13])=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 75799Benzo-1,3-dioxole-5-methylamine

Product 1

HCID 290549N-[(2H-1,3-Benzodioxol-5-yl)methyl]ethanimidic acidYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3,4-methylenedioxybenzylamine (10 g, 66.2 mmol) in acetic acid (50 mL) was added acetic anhydride (15.27 g, 150 mmol). The mixture was stirred at 20° C. for 30 minutes. Then it was adjusted to PH7 with 10% NaOH. The mixture was filtered to obtain a solid which was washed water and dried in vacuum to give N-(benzo[d][1,3]dioxol-5-ylmethyl)acetamide as a white solid (9.24 g, 77%). LC-MS: 194 [M+1]+; 1H-NMR (DMSO-d6): δ 1.84 (s, 3H), 4.12 (d, 2H, J=6.4 Hz), 5.98 (s, 2H), 6.71 (m, 2H), 6.83 (m, 2H), 8.28 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customto obtain a solid which
  3. washwas washed water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-46185baa8e6f4595a312b450072fd88c
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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