Triethylamine → HCID 57443334, compound

HRID 2261806Notes

Reaction equation

HRID 2261806 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[NH2:11].C(N(CC)CC)C.[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[NH:11][C:20](=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 11205965Methyl 2-amino-4-methylbenzoate

Product 1

HCID 57443334HCID 57443334, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-amino-4-methyl-benzoic acid methyl ester (1.5 g, 9.0 mmol) and triethylamine (1.4 g, 13.5 mmol) in methylene chloride (30.0 mL) is added butyryl chloride (1.2 g, 10.8 mmol) dropwise. The mixture is stirred at 0° C. for 30 min and is quenched with saturated sodium bicarbonate (10 mL). The organic phase is washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as syrup (2.2 g, 100%). LC-ES/MS m/e 236.3 (M+1).

Workup

  1. customis quenched with saturated sodium bicarbonate (10 mL)
  2. washThe organic phase is washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-af7ddd3bcafd4b258c2b8e36aab3244c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…