Triethylamine hydrochloride → HCID 178466837, compound

HRID 1096942Notes

Reaction equation

HRID 1096942 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].Cl.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C>[CH2:14]([O:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([C:1]2[NH:18][N:17]=[N:16][N:2]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:15]

Participants

6

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 21942546HCID 21942546, compound

Product 1

HCID 178466837HCID 178466837, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-cyano-5-ethoxybenzoate (182 mg, 0.89 mmol), sodium azide (173 mg, 2.66 mmol), triethylamine hydrochloride (366 mg, 2.66 mmol) and DMF (4.4 mL) was stirred in a nitrogen atmosphere at 100° C. for 12 hours. After left cooled, aqueous 5 N sodium hydroxide solution (0.53 mL, 2.66 mmol) was added to the reaction mixture, and washed with chloroform. The aqueous layer was made to have a pH of 2 with 5 N hydrochloric acid, and extracted with chloroform. The organic layer was dried with sodium sulfate, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to obtain the title compound as a colorless solid.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. washwashed with chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-77615c0e4b284087aed63b72f96d5ab2
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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