Pyridine → HCID 10684544, compound

HRID 842375Notes

Reaction equation

HRID 842375 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]([OH:19])=[O:18])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1>ClCCl>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]2[O:18][C:17](=[O:19])[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 10851968HCID 10851968, compound

Product 1

HCID 10684544HCID 10684544, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[(4-t-butylbenzoyl)amino]-2-thiophenecarboxylic acid (8.09 g, 27 mmol) in dry dichloromethane (135 mL) was added oxalyl chloride (11.8 mL, 135 mmol). The mixture was carefully heated with a heat gun in order to dissolve the starting material and initiate the reaction. The heat was then removed and after stirring for 2 h, the solvents were removed in vacuo. The residue was dissolved in dry dichloromethane (135 mL), and pyridine (2.2 mL, 27 mmol) was added. After 1 h, solvent was removed in vacuo. The residue was partitioned between ethyl acetate and water, and the organic phase was washed four times with water and once with brine. The organic phase was then dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The crude product was purified by column chromatography over silica gel using an eluent of 10% ethyl acetate in hexane to afford the product (7.44 g, 96% yield).

Workup

  1. temperatureThe mixture was carefully heated with a heat gun in order
  2. dissolutionto dissolve the starting material
  3. customthe reaction
  4. customThe heat was then removed
  5. customthe solvents were removed in vacuo
  6. dissolutionThe residue was dissolved in dry dichloromethane (135 mL)
  7. waitAfter 1 h
  8. customsolvent was removed in vacuo
  9. customThe residue was partitioned between ethyl acetate and water
  10. washthe organic phase was washed four times with water
  11. dry with materialThe organic phase was then dried over magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent removed in vacuo
  14. customThe crude product was purified by column chromatography over silica gel using an eluent of 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bd2a2c13161247118fe918990a36ac07
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

Loading…