Water → HCID 22934536, compound

HRID 1354429Notes

Reaction equation

HRID 1354429 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)#[CH:12].C(N(CC)CC)C.O>O1CCCC1>[C:4]1([C:3]2[CH:12]=[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[O:1][N:2]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 640163Methyl 4-ethynylbenzoateHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 22934536HCID 22934536, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (100 ml) of N-hydroxybenzenimidoyl chloride (2.25 g) and methyl 4-ethynylbenzoate (2.30 g) in tetrahydrofuran was added dropwise a solution (10 ml) of triethylamine (2.30 ml) in tetrahydrofuran under an argon atmosphere at 0° C. This mixture was stirred overnight at room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from hexane-tetrahydrofuran to give methyl 4-(3-phenyl-5-isoxazolyl)benzoate (3.49 g, yield 87%) as colorless crystals. melting point: 205–206° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-5d79a94cecf5418c970a07efb2332483
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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