Nitric Acid → HCID 15766514, compound

HRID 2292848Notes

Reaction equation

HRID 2292848 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[CH:4]=1.[N+:11]([O-])([OH:13])=[O:12]>C(OC(=O)C)(=O)C>[CH3:1][S:2][C:3]1[S:7][C:6]2[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[S:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15766513HCID 15766513, compound

Product 1

HCID 15766514HCID 15766514, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
-20 °C

Procedure

1.0 g (5.4 mmol) of 2-methylthiothieno[3,2-b]thiophene is dissolved in 20 ml of acetic anhydride, and the solution is cooled to -20° C. At this temperature, a mixture of 0.6 ml of 70% nitric acid in 5 ml of acetic anhydride is added dropwise. The mixture is then allowed to warm to room temperature. For working up, the mixture is added to ice water end extracted several times with diethyl ether, and the organic phase is washed with saturated sodium hydrogen carbonate solution until neutral and dried with anhydrous magnesium sulfate. After removal of the solvent in a rotary evaporator under reduced pressure, the orange-yellow crude product obtained is purified by preparative column chromatography (SiO2 //2:1 cyclohexane/ethyl acetate, Rf : 0.62) and recrystallized from cyclohexane.

Workup

  1. additionis added dropwise
  2. temperatureto warm to room temperature
  3. extractionextracted several times with diethyl ether
  4. washthe organic phase is washed with saturated sodium hydrogen carbonate solution until neutral and
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customAfter removal of the solvent
  7. customin a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-bb023283ea0a4d20a2d967452297bac8
Source dataset
uspto-grants-1997_11
Patent number
US05684165

Reaction notes

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