Ethyl Acetate → 3-(4-Trifluoromethyl-phenyl)-acrvlovl azide

HRID 1843894Notes

Reaction equation

HRID 1843894 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](Cl)=[O:12])=[CH:5][CH:4]=1.[N-:16]=[N+:17]=[N-:18].[Na+].C(OC(=O)C)C>O1CCOCC1.O.CCCCCC>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([N:16]=[N+:17]=[N-:18])=[O:12])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 542691863-[4-(Trifluoromethyl)phenyl]prop-2-enoyl chloride

Product 1

HCID 860989013-(4-Trifluoromethyl-phenyl)-acrvlovl azideYield 120%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Trifluoromethyl-phenyl)-acryloyl chloride (I-29b: 4.5 g, 0.019 mol) in 1,4-dioxane (20 mL) was added to a stirred mixture of sodium azide (2.7 g, 0.042 mol) in water (10 mL) at 0° C. under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for 20 minutes under nitrogen atmosphere. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was partitioned between water and diethyl ether. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 5.5 g of the crude product which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between water and diethyl ether
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf09a603fe7f4d9c854e90aa8f053195
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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