Sodium hydride → 2-(3-Oxomorpholino)ethyl 2-chloroacetate

HRID 385979Notes

Reaction equation

HRID 385979 reaction equation
[Cl:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][N:8]([CH2:13][CH2:14][OH:15])[C:9](=[O:12])[CH2:10]Cl)=[O:4].[H-].[Na+]>O1CCCC1>[Cl:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:14][O:15][CH2:10][C:9]1=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 152874132-(2-chloro-N-(2-hydroxyethyl)acetamido)ethyl 2-chloroacetate

Product 1

HCID 152873992-(3-Oxomorpholino)ethyl 2-chloroacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
15 °C

Procedure

A solution of 2-(2-chloro-N-(2-hydroxyethyl)acetamido)ethyl 2-chloroacetate (269 g, 1.05 mol) in tetrahydrofuran (250 ml) was added dropwise to a cooled (5° C.) slurry of sodium hydride (50.4 g, 2.10 mol) in tetrahydrofuran (250 ml). To the mixture was then added tetrahydrofuran (3 L). The resulting mixture was allowed to react overnight while the temperature was maintained at 15° C. The mixture was then filtered, and the filtrate was diluted with dichloromethane, washed one time with 500 ml of water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound.

Workup

  1. customto react overnight while the temperature
  2. filtrationThe mixture was then filtered
  3. additionthe filtrate was diluted with dichloromethane
  4. washwashed one time with 500 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67b32d3d897442a487d511f08ecf9386
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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