Oxalyl chloride → HCID 10684544, compound

HRID 428008Notes

Reaction equation

HRID 428008 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>C(Cl)Cl>[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

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 10851968HCID 10851968, compound

Product 1

HCID 10684544HCID 10684544, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-tert-butylbenzoyl)amino-2-thiophenecarboxylic acid (8.1 g, 27 mmol) in methylene chloride (135 mL) was treated with oxalyl chloride (11.8 mL, 135 mmol). The mixture was slowly heated to afford a homogeneous solution. After 2 h, the mixture was concentrated in vacuo and the residue dissolved in methylene chloride (135 mL) and treated with pyridine (2.2 mL). After 1 hr, the mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed four times with water, once with saturated sodium chloride solution, dried (magnesium sulfate), and filtered. Concentration and purification of the residue by flash chromatography (silica gel, hexanes/ethyl acetate) yielded 7.44 g (96%) of the title compound.

Workup

  1. temperatureThe mixture was slowly heated
  2. customto afford a homogeneous solution
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in methylene chloride (135 mL)
  5. additiontreated with pyridine (2.2 mL)
  6. waitAfter 1 hr
  7. concentrationthe mixture was concentrated in vacuo
  8. customthe residue partitioned between ethyl acetate and water
  9. washThe organic layer was washed four times with water
  10. dry with materialonce with saturated sodium chloride solution, dried (magnesium sulfate)
  11. filtrationfiltered
  12. concentrationConcentration and purification of the residue by flash chromatography (silica gel, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-abae8eeec8884ff49c3ddf27b4431c48
Source dataset
uspto-grants-2001_11
Patent number
US06313151B1

Reaction notes

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