Sulfuric Acid → HCID 14719578, compound

HRID 1590842Notes

Reaction equation

HRID 1590842 reaction equation
[CH:1]1[S:5][CH:4]=[CH:3][C:2]=1[CH2:6][NH:7][CH2:8][CH:9](O)[C:10]1[C:15]([F:16])=[CH:14][C:13]([O:17][CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=1.S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[F:16][C:15]1[C:10]([CH:9]2[CH2:8][NH:7][CH2:6][C:2]3[CH:3]=[CH:4][S:5][C:1]2=3)=[CH:11][C:12]([O:19][CH3:20])=[C:13]([O:17][CH3:18])[CH:14]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54536455HCID 54536455, compound

Product 1

HCID 14719578HCID 14719578, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.16 g of α-[[(3-thenyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol was dissolved in 11 ml of trifluoroacetic acid, and after adding thereto 0.31 ml of conc. sulfuric acid under ice cooling, the mixture was stirred for 4 hours. The reaction solution was concentrated, and chloroform and water were added to the residue. The mixture was basified by addition of 10 ml of conc. aqueous ammonia under ice cooling. The chloroform layer was collected after a separating procedure, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized form ethanol, affording 0.76 g of 7-(6-fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, m.p. 108°-111° C.

Workup

  1. additionafter adding
  2. concentrationThe reaction solution was concentrated
  3. additionchloroform and water were added to the residue
  4. additionThe mixture was basified by addition of 10 ml of conc. aqueous ammonia under ice cooling
  5. customThe chloroform layer was collected after a separating procedure
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized form ethanol

Sources & evidence

ORD record
ord-1eef4a89143542769ba069d2b8987286
Source dataset
uspto-grants-1993_04
Patent number
US05204468

Reaction notes

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