Water → HCID 21098732, compound

HRID 1351324Notes

Reaction equation

HRID 1351324 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:11])[NH:9][OH:10])([CH3:6])([CH3:5])[CH3:4].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15].O>CN(C)C=O.O1CCCC1>[C:3]([O:7][C:8](=[O:11])[NH:9][O:10][C:14]([N:13]([CH3:17])[CH3:12])=[O:15])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 21098732HCID 21098732, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (865 mg) in dimethylformamide (12 mL) and tetrahydrofuran (15 mL) was added t-butyl-N-hydroxycarbamate (2.5 g) on an ice bath. After stirring for 30 minutes, dimethylcarbamoyl chloride (2.32 g) was added and was stirred for 1 hour. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The solid that was obtained by drying the organic layer and removing the solvent by evaporation was washed with hexane, and a colorless solid (3.18 g) were obtained.

Workup

  1. stirringwas stirred for 1 hour
  2. extractionthe solution was extracted with ethyl acetate
  3. customThe solid that was obtained
  4. customby drying the organic layer
  5. customremoving the solvent
  6. customby evaporation
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-bc5d2ee67f5c4863b3ab6d673162d102
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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