Hydrochloric Acid → HCID 21100317, compound

HRID 1930981Notes

Reaction equation

HRID 1930981 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][S-:22].[Na+].Cl>CN(C)C=O>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([S:22][CH3:21])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 4378561Sodium methanethiolateHCID 224675662-Fluoro-5-methanesulfonyl-benzoic acid

Product 1

HCID 21100317HCID 21100317, 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 10.0 mmol sodium methanethiolate 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 colourless oil which was used in the next step without further purification (yield 99%). MS (m/e): 244.9 ([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-d5f8aadce7004b2fb16dbf38da80f733
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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