Dimethylformamide → cis-3-Azido-4-oxo-2-azetidinylmethyl bromide

HRID 614452Notes

Reaction equation

HRID 614452 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][C@H:6]1[C@@H:9]([N:10]=[N+:11]=[N-:12])[C:8](=[O:13])[NH:7]1)(=O)=O.[Br-:21].[Li+].CN(C)C=O>C(OCC)(=O)C>[N:10]([C@H:9]1[C:8](=[O:13])[NH:7][C@H:6]1[CH2:5][Br:21])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 82050Lithium BromideHCID 86734335HCID 86734335, compound

Product 1

HCID 86736078cis-3-Azido-4-oxo-2-azetidinylmethyl bromideYield 94.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.413 g (1.40 mmol) of cis-3-azido-4-oxo-2-azetidinylmethyl tosylate, 0.434 g (5.0 mmol) of anhydrous lithium bromide and 5 ml of anhydrous dimethylformamide is heated to 100° under argon for one hour. The solution is allowed to cool to 25°, poured into ethyl acetate and extracted copiously with water. The ethyl acetate layer is dried and evaporated to give 0.270 g (94%) of the title product.

Workup

  1. temperatureis heated to 100° under argon for one hour
  2. temperatureto cool to 25°
  3. extractionextracted copiously with water
  4. dry with materialThe ethyl acetate layer is dried
  5. customevaporated

Sources & evidence

ORD record
ord-b9fc86b063e6454287e7802a7215968b
Source dataset
uspto-grants-1979_03
Patent number
US04144333

Reaction notes

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