Nitric Acid → N-(6-Nitro-1,3-benzodioxol-5-yl)acetamide

HRID 1903147Notes

Reaction equation

HRID 1903147 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)[C:2]([CH3:4])=[O:3].[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[NH:1]([C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamide

Product 1

HCID 540215N-(6-Nitro-1,3-benzodioxol-5-yl)acetamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

56.5 g of 5-acetamino-1,3-benzodioxole in 250 ml of glacial acetic acid were nitrated as described above with a solution of 30 ml of nitric acid in 100 ml of glacial acetic acid in a 500 ml sulfonation flask equipped with stirrer, thermometer and dropping funnel. The crystals, removed by filtration under suction, were washed thoroughly with water and dried overnight at about 60° C. in vacuo. There were obtained 68.3 g (96.6% of theory) of 5-acetamino-6-nitro-1,3-benzodioxole of melting point 211°-213° C.

Workup

  1. customequipped with stirrer
  2. customThe crystals, removed by filtration under suction
  3. washwere washed thoroughly with water
  4. customdried overnight at about 60° C. in vacuo

Sources & evidence

ORD record
ord-096baff005934ad99828c1baf3446c7e
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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