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

HRID 577613

Reaction equation

HRID 577613 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[CH3:11][C:12](OC(C)=O)=[O:13].C([O-])(O)=O.[Na+]>CC(O)=O>[O:10]1[C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:13])[CH3:11])=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 843101,3-Benzodioxol-5-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3,4-(Methylenedioxy)aniline (8 g, 58.3 mmol) in AcOH (120 ml) was added Ac2O (48 mL). The mixture was stirred for overnight. After reaction, the mixture was poured into saturated NaHCO3 solution, and then filtered. The filtrate was extracted with ethyl acetate to give N-(benzo[d][1,3]dioxol-5-yl)acetamide (10 g, 95%). LCMS: 180[M+1]+.; 1H NMR (DMSO-d6) δ 2.0 (s, 3H), 5.96 (s, 2H), 6.82 (d, 1H, J=8.1 Hz), 6.91 (d, 1H, J=2.1 Hz), 7.30 (d, 1H, J=1.8 Hz), 9.84 (s, 1H).

Workup

  1. customAfter reaction
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate

Sources & evidence

ORD record
ord-7c9ba336153c4c0a9a4ba7e7418b721d
Source dataset
uspto-grants-2015_05
Patent number
US09040556B2

Linked notes

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