Sulfuric Acid → HCID 86698277, compound

HRID 2408961Notes

Reaction equation

HRID 2408961 reaction equation
[C:1]([C:5]1[Se:9][C:8]([C:10]#[N:11])=[C:7]([OH:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:13]S(O)(=O)=O>FC(F)(F)C(O)=O>[C:1]([C:5]1[Se:9][C:8]([C:10]([NH2:11])=[O:13])=[C:7]([OH:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86698278HCID 86698278, compound

Product 1

HCID 86698277HCID 86698277, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To an ice cold solution of 5-tert-butyl-3-hydroxyselenophene-2-carbonitrile (0.5 g) in trifluoroacetic acid (2 mL) was added H2SO4 (0.5 mL) dropwise for 15 min. The reaction mixture was allowed to rt and stirred for 6 h. The reaction mixture was poured into ice cold water extracted with chloroform (3×50 mL). The combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (75:25) as eluents to give the product as a brown color solid (460 mg, 86%), mp 164-168° C. 1H NMR (400 MHz, CDCl3): δ 11.53 (1H, br s), 6.81 (1H, s), 5.35 (2H, s), 1.35 (9H, s); LC-MS (negative ion mode): m/z 244, 246 (M−H)−.

Workup

  1. customwas allowed to rt
  2. additionThe reaction mixture was poured into ice cold water
  3. extractionextracted with chloroform (3×50 mL)
  4. washThe combined chloroform layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated the solvent
  8. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-0b732329e63542be8e14e00b5b2090bf
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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