Dimethylformamide → HCID 19096639, compound

HRID 1657201Notes

Reaction equation

HRID 1657201 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CN(C=O)C.[CH3:10][C:11]1([CH3:23])[O:16][C:15](=[O:17])[CH:14]=[C:13]([CH2:18][C:19](=[O:22])[CH2:20]Cl)[O:12]1>C(OCC)(=O)C>[CH3:10][C:11]1([CH3:23])[O:16][C:15](=[O:17])[CH:14]=[C:13]([CH2:18][C:19](=[O:22])[CH2:20][N:1]=[N+:2]=[N-:3])[O:12]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 149448286-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-one

Product 1

HCID 19096639HCID 19096639, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

195 mg (3.0 mmol) of sodium azide were added to 2 ml of a DMF solution containing 328 mg (1.5 mmol) of 2,2-dimethyl-6-(3-chloro-2-oxopropyl)-1,3-dioxin-4-one prepared in Example 1, followed by stirring at room temperature for 10 minutes. Afterward, the solution was poured into ice water, extracted with ether, and then dried with anhydrous magnesium sulfate. After ether was distilled off, the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=1:1), thereby obtaining 278 mg (yield 82%) of 2,2-dimethyl-6-(3-azido-2-oxopropyl)-1,3-dioxin-4-one.

Workup

  1. extractionextracted with ether
  2. dry with materialdried with anhydrous magnesium sulfate
  3. distillationAfter ether was distilled off

Sources & evidence

ORD record
ord-28c6f3cbbc37419ba606fc6727ae7467
Source dataset
uspto-grants-1993_10
Patent number
US05256800

Reaction notes

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