Hydrochloric Acid → HCID 21100235, compound

HRID 225700Notes

Reaction equation

HRID 225700 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][CH:22]([CH3:25])[CH2:23][SH:24].Cl>CN(C)C=O>[CH2:23]([S:24][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH:22]([CH3:25])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10558Isobutyl mercaptanHCID 10796Cesium carbonateHCID 224675662-Fluoro-5-methanesulfonyl-benzoic acid

Product 1

HCID 21100235HCID 21100235, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4.58 mmol 2-fluoro-5-methanesulfonyl-benzoic acid (Example B4(b)) in 6 ml N,N-dimethylformamide were added 13.8 mol cesium carbonate and 9.97 mmol 2-methyl-1-propanethiol and the mixture was stirred at 90° C. for 30 min. The reaction mixture was then cooled to room temperature and acidified to pH1 by addition of hydrochloric acid before being extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid which was used in the next step without further purification (yield 99%). MS (m/e): 287.0 ([M−H]−, 100%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionbefore being extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ca9de5ee03f4d3db0519f21ed614871
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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