Hydrochloric Acid → HCID 22934522, compound

HRID 1354430Notes

Reaction equation

HRID 1354430 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[N:9][OH:10])=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)#[CH:13].C(N(CC)CC)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 640163Methyl 4-ethynylbenzoateHCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Product 1

HCID 22934522HCID 22934522, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (70 ml) of 4-chloro-N-hydroxybenzenimidoyl chloride (3.28 g) and methyl 4-ethynylbenzoate (3.00 g) in tetrahydrofuran was added dropwise a solution (5 ml) of triethylamine (2.8 ml) in tetrahydrofuran under an argon atmosphere at 0° C. This mixture was stirred overnight at room temperature and poured into dilute hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, volume ratio) to give methyl 4-[3-(4-chlorophenyl)-5-isoxazolyl]benzoate (4.40 g, yield 81%). Recrystallization from hexane-acetone gave colorless prism crystals. melting point: 225–226° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, volume ratio)

Sources & evidence

ORD record
ord-d00d607fdbf54f349841a2b83343eebe
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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