Ethyl Acetate → 3-Chloro-2,2-dimethyl-propionyl azide

HRID 80270

Reaction equation

HRID 80270 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8](Cl)=[O:9].C(OC(=O)C)C>O1CCOCC1.O.CCCCCC>[Cl:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8]([N:1]=[N+:2]=[N-:3])=[O:9]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 1

HCID 596361603-Chloro-2,2-dimethyl-propionyl azideYield 61.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium azide (4.64 g, 71.38 mmol) was added to a solution of 3-chloro-2,2-dimethyl-propionyl chloride (I-200a: 6 g, 35.71 mmol) in 1,4-dioxane (15 mL) and water (15 mL). The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (5% ethylacetate in hexane). The reaction mixture was extracted with diethyl ether and the organic layer was dried over Na2SO4 to afford 3.5 g of the product (61.40% yield).

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. dry with materialthe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-61aeecbee34f43d2baa40b2c427cbaf5
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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