Hydrochloric Acid → HCID 22248020, compound

HRID 606173

Reaction equation

HRID 606173 reaction equation
C1(OP([CH:17](NC2C=CC=CC=2)[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)(=O)OC2C=CC=CC=2)C=CC=CC=1.[F:31][C:32]1[C:33]([CH:37]=O)=[CH:34][S:35][CH:36]=1.C(=O)([O-])[O-:40].[Cs+].[Cs+].Cl.[OH-].[Na+]>O1CCCC1CCCO>[F:31][C:32]1[C:33]([CH2:37][C:17]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[O:40])=[CH:34][S:35][CH:36]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 423769diphenyl (phenylamino)(pyridin-4-yl)methylphosphonateHCID 22247846614729-75-8

Product 1

HCID 22248020HCID 22248020, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 130202-Furanpropanol, tetrahydro-Solvent

Procedure

After dissolving 19.6 g of [(phenylamino)-(4-pyridylmethyl)]phosphonic acid diphenyl ester [CAS No. 3360-72-3] in 115 ml of tetrahydrofuran-2-propanol (4:1), 6.02 g of 4-fluorothiophene-3-carboxaldehyde and 19.61 g of anhydrous cesium carbonate were added and the mixture was stirred overnight at room temperature. Next, 90 ml of 5N hydrochloric acid was added to the reaction mixture and the mixture was stirred at room temperature for 6 hours. After adding a 5N sodium hydroxide solution to the reaction solution, extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate). The obtained solid was washed with n-hexane to obtain the title compound (3.66 g, 36% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. extractionto the reaction solution, extraction
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)
  7. washThe obtained solid was washed with n-hexane

Sources & evidence

ORD record
ord-d2a94cafe5934610ae758e1365af29c7
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Linked notes

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