Triethylamine → 1,1,1-Trifluoro-N-phenylmethanesulfonamide

HRID 1369285Notes

Reaction equation

HRID 1369285 reaction equation
[CH:1]([C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:14]([O:16][CH3:17])=[O:15])=[O:2].CCN(CC)CC.[C:25]1([N:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.CCOCC>[C:25]1([NH:31][S:32]([C:35]([F:38])([F:36])[F:37])(=[O:34])=[O:33])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1.[CH:1]([C:3]1[C:12]([O:13][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:14]([O:16][CH3:17])=[O:15])=[O:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 142176Phenyl triflimideHCID 18519041HCID 18519041, compound

Product 2

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideYield 90%HCID 18519038HCID 18519038, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-formyl-6-hydroxy-1-naphthoate (500 mg, 2.17 mmol) in CH2Cl2 (10.2 mL) at rt was added Et3N (483 mg, 4.78 mmol, 0.664 mL) followed by PhNTf2 (928 mg, 2.6 mmol). The mixture was stirred for 18 h and then diluted with Et2O and washed with 1.0 M HCl. The extract was dried with MgSO4 and concentrated in vacuo. The crude material was chromatographed on silica gel (20:1 hexanes/EtOAc), and the material thus obtained was recrystallized from hexanes to give 1.0 g of a 3:2 mixture of the title compound and PhNHTf (˜90% yield).

Workup

  1. washwashed with 1.0 M HCl
  2. dry with materialThe extract was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was chromatographed on silica gel (20:1 hexanes/EtOAc)
  5. customthe material thus obtained
  6. customwas recrystallized from hexanes
  7. customto give

Sources & evidence

ORD record
ord-960298218b2b42ff988a9ea11e221d25
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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