Triethylamine → 5-(3-Hydroxyphenyl)-3-(pyridin-2-yl)-1,2-oxazole

HRID 2216796Notes

Reaction equation

HRID 2216796 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](Cl)=[N:8][OH:9].[OH:11][C:12]1[CH:13]=[C:14]([C:18]#[CH:19])[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:11][C:12]1[CH:13]=[C:14]([C:18]2[O:9][N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139144m-EthynylphenolHCID 421736N-hydroxy-2-pyridinecarboximidoyl chloride

Product 1

HCID 98812045-(3-Hydroxyphenyl)-3-(pyridin-2-yl)-1,2-oxazoleYield 44.2%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A stirred solution of pyridine-2-carbohydroximoyl chloride (300 mg, 1.9 mmol) and 3-hydroxyphenylacetylene (760 mg, 6.4 mmol) in a 1:1 mixture of THF/CH2Cl2 (10 mL) at 0° C. was treated with triethylamine (2 mL, 1.45 g, 15 mmol). The mixture was allowed to warm to room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with brine and dried over anhydrous sodium sulphate. Removal of the solvent in vacuo followed by trituation with 10% ethylacetate in hexane afforded 200 mg (44%) of 5-[3-hydroxyphenyl]-3-[pyridin-2-yl]-1,2-oxazole as a beige solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-9cf9a4eac9fc479c99635a56ce326a90
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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