Thionyl Chloride → HCID 60715543, compound

HRID 1473817Notes

Reaction equation

HRID 1473817 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([F:25])[CH:19]=1>O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=2[OH:1])=[C:20]([F:25])[CH:19]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 752314-Methoxysalicylic AcidHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 60715543HCID 60715543, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-hydroxy-4-methoxybenzoic acid (1.68 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 4-chloro-2-fluorobenzenamine (1.1 mL, 10 mmole) in THF (40 mL) for 14 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-d1dbf12fd4c547e68fd02df3dbc10ea5
Source dataset
uspto-grants-2015_04
Patent number
US09018203B2

Reaction notes

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