Hydrochloric Acid → HCID 59191299, compound

HRID 1023942Notes

Reaction equation

HRID 1023942 reaction equation
[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][CH:15]=O)=[C:5]([O:19][CH3:20])[CH:4]=1)[CH3:2].Cl>C1COCC1.CO>[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][CH3:15])=[C:5]([O:19][CH3:20])[CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59191252HCID 59191252, compound

Product 1

HCID 59191299HCID 59191299, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[2-(4-ethyl-2-methoxyphenoxy)phenyl]formamide (0.21 mmol; 72 mg), under argon, in dry THF was added at 0° C., borane dimethylsulfide complex (0.51 mmol, 49 μL). The reaction was stirred at reflux for 3 h 30. After cooling to 0° C., the mixture was diluted with 1 mL of dry methanol and stirred 1 hour. HCl (4M in dioxane) was added at 0° C. until pH 2, then the mixture was refluxed 1 hour. After cooling to room temperature, the reaction was diluted with 5 mL of methanol and concentrated in vacuo. The crude was treated with 5 mL of NaOH (1N), until pH 12, and extracted with ethyl acetate (3*2mL). Combined organic phases were dried over Na2SO4 and concentrated in vacuo to yield the title compound (66 mg, quantitative) as a red oil used without further purification.

Workup

  1. temperatureat reflux for 3 h 30
  2. stirringstirred 1 hour
  3. temperaturethe mixture was refluxed 1 hour
  4. temperatureAfter cooling to room temperature
  5. concentrationconcentrated in vacuo
  6. additionThe crude was treated with 5 mL of NaOH (1N), until pH 12
  7. extractionextracted with ethyl acetate (3*2mL)
  8. dry with materialCombined organic phases were dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-390bcc38865b4a9eb347434021b8d4a9
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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