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

HRID 2189252Notes

Reaction equation

HRID 2189252 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-d02619ec5ccc484dadcbaeaa1031a919
Source dataset
uspto-grants-2012_12
Patent number
US08324240B2

Reaction notes

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