Sulfuric Acid → HCID 18691297, compound

HRID 376312Notes

Reaction equation

HRID 376312 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=[C:11]([CH3:18])[N:10]=2)=CC=1.S(=O)(=O)(O)O.O.N>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:14]2[CH:15]=[CH:16][S:17][C:13]=2[CH:12]=[C:11]([CH3:18])[N:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12896473Azane;hydrateHCID 18691200HCID 18691200, compound

Product 1

HCID 18691297HCID 18691297, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 24 g of 4-(4-methoxybenzyl)amino-6-methylthieno[3,2-c]pyridine in 80 ml of trifluoroacetic acid was added 15 ml of concentrated sulfuric acid, and the mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was poured into ice water, rendered alkaline by the addition of 28% ammonia water and extracted with chloroform. The extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel and recrystallized from chloroform/petroleum ether to give 15 g of the title compound as a white powder.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. customrecrystallized from chloroform/petroleum ether

Sources & evidence

ORD record
ord-71d72151024f48c3a2d6bb561229a9db
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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