Nitric Acid → HCID 86740693, compound

HRID 483101Notes

Reaction equation

HRID 483101 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)#[N:2].[N+:8]([O-:11])([OH:10])=[O:9]>S(=O)(=O)(O)O>[C:1]([C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1)#[N:2].[C:1]([C:3]1[S:4][CH:5]=[C:6]([N+:8]([O-:11])=[O:9])[CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 660872-Thiophenecarbonitrile

Product 1

HCID 86740693HCID 86740693, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 10 ml conc. sulfuric acid stirred at 0° C. was added 2-cyano-thiophene (4.0 g, 0.036 mole). Six mililiters of a mixture of 1:1 conc. sulfuric acid and fuming nitric acid was added dropwise to the solution and the temperature was maintained between 10° C. and 15° C. The reaction mixture was allowed to warm-up to room temperature after addition was completed and was stirred for an additional hour. The dark red solution was quenched with 50 ml of ice water and stirred vigorously. A yellow solid precipitated out. The solid was collected on a filter and washed with ice water (2×5 ml). This solid weighed 3.7 g (66%) and is a mixture of 4- & 5-nitro 2-cyano thiophene with 1:2 ratio.

Workup

  1. additionwas added dropwise to the solution
  2. temperaturethe temperature was maintained between 10° C. and 15° C
  3. additionafter addition
  4. customThe dark red solution was quenched with 50 ml of ice water
  5. stirringstirred vigorously
  6. customA yellow solid precipitated out
  7. customThe solid was collected on
  8. filtrationa filter
  9. washwashed with ice water (2×5 ml)
  10. additiona mixture of 4- & 5-nitro 2-cyano thiophene with 1:2 ratio

Sources & evidence

ORD record
ord-38b2052bbe064dfeb9946d3b6d86c355
Source dataset
uspto-grants-1986_03
Patent number
US04578390

Reaction notes

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