Sodium Carbonate → HCID 178449972, compound

HRID 1433180Notes

Reaction equation

HRID 1433180 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:25]=[CH:24][C:18]2[NH:19][C:20]([CH2:22]Cl)=[N:21][C:17]=2[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:25]=[CH:24][C:18]2[NH:19][C:20]([CH2:22][O:34][C:31]3[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:35])[F:36])=[CH:33][CH:32]=3)=[N:21][C:17]=2[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 178449971HCID 178449971, compound

Product 1

HCID 178449972HCID 178449972, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-tert-butyl-2-(2-chloromethyl-1H-benzoimidazol-5-yl)benzenesulfonamide (100 mg, 0.26 mmol), α,α,α-trifluoro-p-cresol (43.0 mg, 0.26 mmol), Na2CO3 (28.1 mg, 0.26 mmol), Cs2CO3 (86.5 mg, 0.26 mmol), and catalytic KI (1.5 mg, 0.009 mmol) in acetone (2 mL) was refluxed for 12 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography (silica, EtOAc: hexanes, 1:1) to afford the title compound as an off-white solid (40.1 mg, 30% yield). Calcd. For C25H24F3N3O3S: 504.54 (M+H), Found 504.2.

Workup

  1. temperaturewas refluxed for 12 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by chromatography (silica, EtOAc: hexanes, 1:1)

Sources & evidence

ORD record
ord-ac4398f35721440c8b4a62709c4f140c
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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