Hydrochloric Acid → HCID 11429986, compound

HRID 1369074Notes

Reaction equation

HRID 1369074 reaction equation
[C:1]([O:7]C)(=O)[C:2]([O:4][CH3:5])=[O:3].C[O-].[Na+].[I:12][C:13]1[CH:14]=[C:15]([N+:24]([O-:26])=[O:25])[C:16]([CH3:23])=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.Cl>CO>[N+:24]([C:15]1[CH:14]=[C:13]([I:12])[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[C:16]=1[CH2:23][C:1](=[O:7])[C:2]([O:4][CH3:5])=[O:3])([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11120Dimethyl oxalateHCID 10942334Sodium MethoxideHCID 11198316HCID 11198316, compound

Product 1

HCID 11429986HCID 11429986, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl oxalate (127.79 g, 5.0 eq) was added to sodium methylate (216.4 mL, 28%, 5.0 eq). The resulting mixture was stirred at room temperature for 1.5 hours. To the mixture was then added 5-iodo-2-methyl-3-nitrobenzotrifluoride (71.64 g, 216.4 mmol), dissolved in MeOH (216 mL). The dark red mixture was then stirred at room temperature for 6 hours and left over night. The solvent was removed in vacuo to give a red solid which was subsequently added to aqueous 2.5N HCl (800 mL). The mixture was extracted with EtOAc (500 mL and 2×300 mL). The extracts were combined and dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to give a yellow solid of the crude product (161.41 g). A fraction of this was purified by column chromatography (silica gel, eluting 15:1 to 10:1 hexane:EtOAc) to give the title compound as a yellow solid.

Workup

  1. stirringThe dark red mixture was then stirred at room temperature for 6 hours
  2. waitleft over night
  3. customThe solvent was removed in vacuo
  4. customto give a red solid which
  5. extractionThe mixture was extracted with EtOAc (500 mL and 2×300 mL)
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationAfter filtration
  8. customthe solvent was removed in vacuo
  9. customto give a yellow solid of the crude product (161.41 g)
  10. customA fraction of this was purified by column chromatography (silica gel, eluting 15:1 to 10:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-82fa6e7c8a5643158d76780517a49d79
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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