Salicylic Acid → HCID 28393775, compound

HRID 1473821Notes

Reaction equation

HRID 1473821 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].S(Cl)(Cl)=O.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH2:23]>O1CCCC1>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 97092,4-DifluoroanilineHCID 24386Thionyl Chloride

Product 1

HCID 28393775HCID 28393775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of salicylic acid (1.38 g, 10 mmole) in tetrahydrofuran (40 mL) was added thionyl chloride (2.5 mL, 35 mmole) and refluxed 3 hr. The mixture was steamed (110° C.) by Dean-Stark. The residue was directly reacted with 2,4-difluorobenzenamine (1 mL, 10 mmole) in THF (40 mL) for 3 hr. The reaction mixture was concentrated and extracted with ethyl acetate, dried over anhydrous magnesium sulfate. Recrystallization of desired products from hot dichloromethane afforded the compound.

Workup

  1. temperaturerefluxed 3 hr
  2. custom(110° C.)
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRecrystallization of desired products from hot dichloromethane
  7. customafforded the compound

Sources & evidence

ORD record
ord-3a99419fbd7a4b9eabd82d706d9bc970
Source dataset
uspto-grants-2015_04
Patent number
US09018203B2

Reaction notes

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