Ethylamine → HCID 669440, compound

HRID 2390517Notes

Reaction equation

HRID 2390517 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:12][CH2:13][N:14](CC)CC.C(N)C>C(Cl)Cl>[CH2:13]([NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 74374m-Anisoyl chloride

Product 1

HCID 669440HCID 669440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxybenzoyl chloride (commercially available from Aldrich, 5 mL, 35 mol) and Et3N (10 mL) in 100 mL of DCM was added and EtNH2 (2 M/THF, 30 mL, 60 mmol) dropwise for 30 min at 0° C. and the resulting solution was stirred for additional 1 h. The reaction mixture was washed with aq. NaHCO3 and brine, consecutively. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding oily residue, which was subjected to column chromatography to yield Example A175a (6.2 g, >95%) as a colorless oil.

Workup

  1. washThe reaction mixture was washed with aq. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customyielding oily residue, which
  5. customto yield Example A175a (6.2 g, >95%) as a colorless oil

Sources & evidence

ORD record
ord-3ffa9742fedb42da974fff19497a6220
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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