Sodium hydride → HCID 15916920, compound

HRID 1995908Notes

Reaction equation

HRID 1995908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[H][H].S(O[CH2:24][CH2:25][O:26][CH2:27][CH:28]1[CH2:30][CH2:29]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:24][CH2:25][O:26][CH2:27][CH:28]2[CH2:30][CH2:29]2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 8198212-Chloro-5-hydroxypyridineHCID 15916919HCID 15916919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15916920HCID 15916920, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 12.9 g (0.1 mol) of 2-chloro-5-hydroxypyridine in 50 cc of dry dimethylformamide is added to a suspension of 4.8 g (0.1 mol) of sodium hydride (a 50% dispersion in mineral oil) in 200 cc of dimethylformamide. When the evolution of hydrogen has ceased, a solution of 27 g (0.1 mol) of 2-cyclopropylmethoxy-ethanol tosylate in 50 cc of dimethylformamide is added and the mixture is heated at 50°-60° C. for 5 hours. It is then cooled and poured into water; extraction is carried out with diethyl ether and the organic phase is washed with water. After drying, filtration and evaporation of the ether phase, an oil is obtained, which is distilled. Its boiling point (0.1 mm Hg) is 136° C.

Workup

  1. temperaturethe mixture is heated at 50°-60° C. for 5 hours
  2. temperatureIt is then cooled
  3. extractionextraction
  4. washthe organic phase is washed with water
  5. customAfter drying
  6. filtrationfiltration and evaporation of the ether phase
  7. customan oil is obtained
  8. distillationwhich is distilled
  9. customis 136° C.

Sources & evidence

ORD record
ord-87816cc5a8624a98b055a887a2853ab5
Source dataset
uspto-grants-1983_09
Patent number
US04406907

Reaction notes

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