HCID 10035507, compound → Benzofuroxan

HRID 1683162Notes

Reaction equation

HRID 1683162 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N+]=[N-])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1>C1(C)C=CC=CC=1>[CH:8]1[CH:3]=[CH:4][C:5]2[C:6](=[N:9][O:13][N+:12]=2[O-:14])[CH:7]=1

Participants

3

Reactant 1

HCID 10035507HCID 10035507, compound

Product 1

HCID 68075BenzofuroxanYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the 4-methoxy-2-nitrophenylazide (5.06 g, 26.1 mmol) and 7.8 mL of fleshly distilled toluene was heated to 110° C. for three hours and then cooled to 95° C. and stirred for an additional two hours. The toluene was removed in vacuo to give a brown solid. The crude product was recrystallized from methanol to yield 3.35 g (77% yield) of benzofuroxan as orange-brown crystals (m.p. 114°-115° C.). Rf 0.30 in 20% ethyl acetate/hexane. 1HNMR (CDCl3) δ 6.19 7.45 (m, 3H), 3.89 (s, 3H).

Workup

  1. temperaturecooled to 95° C.
  2. customThe toluene was removed in vacuo
  3. customto give a brown solid
  4. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-ad4cbf9c067244cd9bc686cf42918f69
Source dataset
uspto-grants-1997_06
Patent number
US05637591

Reaction notes

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