Imidazole → HCID 11611723, compound

HRID 749641Notes

Reaction equation

HRID 749641 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH:5]=[CH:4][C:3]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 59753133HCID 59753133, compound

Product 1

HCID 11611723HCID 11611723, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

50 mg 2-[4-(2-Chloro-4-fluoro-benzenesulfonyl)phenyl]-1,1,1-trifluoropropan-2-ol (0.13 mmol) was combined in a pressure tube with 50 mg imidazole. The resulting mixture was then placed into a preheated 100° C. bath. After stirring for 12 h, the mixture was diluted with CH2Cl2 and sat. NaHCO3, then extracted (3×10% MeOH/CH2Cl2). The organics were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 3-5% MeOH/CH2Cl2) gave 60 mg of the product as a white solid (0.13 mmol, quant.). 1H NMR (DMSO-d6, 400 MHz) δ 8.49 (s, 1H), 8.39 (d, J=8.7 Hz, 1H), 8.1 (d, J=2.2 Hz, 1H), 8.02 (dd, J=2.2 Hz, 8.7 Hz, 1H), 7.99 (d, J=8.7 Hz, 2H), 7.94 (s, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.16 (s, 1H), 6.91 (s, 1H), 1.71 (s, 3H).

Workup

  1. customwas then placed into a preheated 100° C.
  2. extractionextracted (3×10% MeOH/CH2Cl2)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (SiO2, 3-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-173d43d7491b414e9ff3641a9eff2d17
Source dataset
uspto-grants-2008_07
Patent number
US07402704B2

Reaction notes

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