Water → HCID 57963295, compound

HRID 1690024Notes

Reaction equation

HRID 1690024 reaction equation
[NH2:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>ClCCl>[F:11][C:3]1[C:2]([NH:1][S:26]([C:23]2[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:30])[F:31])=[CH:25][CH:24]=2)(=[O:28])=[O:27])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 230943433-Amino-2-fluorobenzoic acid

Product 1

HCID 57963295HCID 57963295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-amino-2-fluoro-benzoic acid (29, 1.70 g, 11 mmol) in 34 mL of dichloromethane, pyridine (2.2 mL, 27 mmol) and 4-trifluoromethyl-benzenesulfonyl chloride (30, 6.7 g, 27 mmol) were added. The reaction was stirred at room temperature overnight, then poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound 31 as a white solid, which was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-ae6a30bb3f35494c94558c2b21724112
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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