N-(1,1-dimethyl-2-propynyl)benzamide → HCID 15411099, compound

HRID 1107058Notes

Reaction equation

HRID 1107058 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:5])[C:3]#[CH:4]>[N+]([O-])([O-])=O.[Ag+].C(OCCCC)(=O)C>[CH3:5][C:2]1([CH3:1])[C:3](=[CH2:4])[O:14][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6]1

Participants

4

Reactant 1

HCID 36391N-(1,1-dimethyl-2-propynyl)benzamide

Product 1

HCID 15411099HCID 15411099, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 31272Butyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A round bottom flask was charged with N-(3-methylbutyn-3-yl)benzamide (5.0 g, 26.7 mmol), silver nitrate (9.1 mg, 0.2 mol %), and n-butyl acetate (20 mL). The resulting mixture was heated to 95° C. for 0.5 h, then cooled to room temperature. The reaction was washed with water, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was dried in a vacuum oven to give 4,4-dimethyl-5-methylene-2-phenyloxazoline (4.67 g 93% yield) as a pale yellow oil (bp 70-75° C., 0.6 mm Hg).

Workup

  1. temperaturecooled to room temperature
  2. washThe reaction was washed with water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customThe residue was dried in a vacuum oven

Sources & evidence

ORD record
ord-88b5c0e3190a48b881751aedbd95d9de
Source dataset
uspto-grants-2000_05
Patent number
US06057477

Reaction notes

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