Sodium Hydroxide → HCID 57867427, compound

HRID 1960082Notes

Reaction equation

HRID 1960082 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([CH2:13]O)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:17])=O.N1C2C=CC=CC=2N=N1.[OH-].[Na+]>O.O1CCCC1.CN(C)C(=O)C>[Cl:17][CH2:13][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[O:12][N:11]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 44159846HCID 44159846, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 57867427HCID 57867427, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of [5-(2-aminopyridin-3-yl)isoxazol-3-yl]methanol (0.19 g, 1 mmol) and N,N-dimethyl acetamide (1 mL) was added a mixture of thionyl chloride (0.15 mL, 2 mmol), benzotriazole (0.26 g, 2.2 mmol) and tetrahydrofuran (1 mL) under an ice cooling, which was stirred at room temperature for 30 minutes. To the reaction mixture were added water and 5N aqueous sodium hydroxide to adjust basic, then extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride water. The solvent was evaporated under a reduced pressure, so as to obtain the title compound (0.21 g) as a pale yellow solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated sodium chloride water
  4. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-3e07c5a1fa0a4728aab85a386df24877
Source dataset
uspto-grants-2013_04
Patent number
US08410277B2

Reaction notes

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