Sodium hydride → HCID 20301102, compound

HRID 1733293Notes

Reaction equation

HRID 1733293 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH:7][C:8](=[O:10])[CH3:9])[CH:3]=1.[H-].[Na+].Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl>CN(C)C=O>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][N:7]([C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1)[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 538625N-(5-methylisoxazol-3-yl)acetamideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 20301102HCID 20301102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction is run under a nitrogen atmosphere. To a stirred solution of 14.0 g. (0.10 mole) of N-(5-methyl-3-isoxazolyl)acetamide in 100 ml. of dry dimethyl formamide is added 4.3 g. (0.10 ml.) of the 56% sodium hydride suspension. An immediate reaction occurs and solids begin to separate (temperature rises to 55° C.). Then 15.8 g. (0.11 mole) of 2-dimethylaminoethyl chloride hydrochloride is added portionwise along with an additional 4.3 g. (0.11 mole) of sodium hydride (temperature rises to 75°-85° C.). The mixture is stirred for 15 minutes until the temperature begins to fall and is then heated on the steam bath for 28 hours. The dark mixture is filtered to remove precipitated salts, and the dark filtrate is concentrated under reduced pressure at 80°-90° C. This affords 21.7 g. of dark liquid which is dissolved in 150 ml. of ether, filtered through charcoal and concentrated to give 19.0 g. of pale yellow liquid which is used as is in the next step.

Workup

  1. customAn immediate reaction
  2. customto separate (temperature rises to 55° C.)
  3. temperatureis then heated on the steam bath for 28 hours
  4. filtrationThe dark mixture is filtered
  5. customto remove
  6. customprecipitated salts
  7. concentrationthe dark filtrate is concentrated under reduced pressure at 80°-90° C
  8. dissolutionof dark liquid which is dissolved in 150 ml
  9. filtrationof ether, filtered through charcoal
  10. concentrationconcentrated
  11. customto give 19.0 g

Sources & evidence

ORD record
ord-26fae26399ef4e2e802ce2f00f9a66ec
Source dataset
uspto-grants-1980_12
Patent number
US04241072

Reaction notes

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