Triethylamine → HCID 18630857, compound

HRID 1060188Notes

Reaction equation

HRID 1060188 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].CS(O)(=O)=O.[C:23]1([CH2:29][CH:30]2[NH:34][CH2:33][C:32](=[O:35])[CH2:31]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:34]1[CH:30]([CH2:29][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:31][C:32](=[O:35])[CH2:33]1)=[O:7]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 18630836HCID 18630836, compound

Product 1

HCID 18630857HCID 18630857, compoundYield 12.5%

Procedure

3,5-di(trifluoromethyl)benzoyl chloride (0.03 mol) was added to intermediate 23 (0.027 mol). The mixture was stirred and triethylamine (0.1 mol) was added. The mixture was stirred at RT for 18 hours and then washed with water, NaOH and a saturated NaCl solution. The organic layer was separated, washed with a saturated NaCl solution, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 1.4 g of (±)-1-[3,5-bis(trifluoromethyl)benzoyl]-5-(phenylmethyl)-3-pyrrolidinone (intermnediate 24).

Workup

  1. stirringThe mixture was stirred at RT for 18 hours
  2. washwashed with water, NaOH
  3. customThe organic layer was separated
  4. washwashed with a saturated NaCl solution
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e76b35bcf6504608bab3599623919de7
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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