Water → HCID 18630027, compound

HRID 374963Notes

Reaction equation

HRID 374963 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].F[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].[OH2:16].[CH2:17](I)[CH3:18]>C(O)(C)(C)C>[CH2:17]([NH:11][C:10](=[O:16])[C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[O:4][C:2]([CH3:5])([CH3:3])[CH3:1])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 678552-FluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 18630027HCID 18630027, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a slurry of potassium t-butoxide (56.0 g, 0.5 mol) in t-butanol (200 mL) at room temperature was added 2-fluorobenzonitrile (12.1 g, 0.1 mol). The reaction mixture was heated to reflux for 30 min and water (3.6 mL, 0.2 mol) was added. The reaction was heated at reflux for 2 h and ethyl iodide (40 mL, 0.5 mol) was added portionwise over 40 min as reflux was continued. After cooling and stirring at room temperature overnight, GC and GC MS analysis of the reaction indicated a 61% yield of N-ethyl 2-[(1,1-dimethylethyl)oxy]benzamide. Thus, using appropriate analogous conditions the compounds of this invention can be made in a one pot process.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 2 h
  5. temperatureas reflux
  6. temperatureAfter cooling

Sources & evidence

ORD record
ord-f3557f0747da46c1a57833faec2a9d7d
Source dataset
uspto-grants-1996_01
Patent number
US05482974

Reaction notes

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