Triethylamine → HCID 58805186, compound

HRID 884437Notes

Reaction equation

HRID 884437 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[OH:11].C(N(CC)CC)C.[N:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(Cl)(Cl)Cl>[OH:11][C:5]1[CH:6]=[C:7]([NH:10][C:26]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:27])[CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77787Methyl p-aminosalicylateHCID 848104-Morpholinecarbonyl chloride

Product 1

HCID 58805186HCID 58805186, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-amino-2-hydroxy-benzoic acid methyl ester (1.0 g, 6 mmol) and triethylamine (0.8 mL, 6 mmol) in CHCl3 (25 mL) was treated with morpholine-4-carbonyl chloride (4.2 mL, 48 mmol) and stirred at reflux for 72 h. After cooling to room temperature, the solution was washed with 5% aqueous hydrochloric acid (25 mL), saturated aqueous sodium bicarbonate (25 mL), and brine (25 mL), dried over Na2SO4, and concentrated to an orange solid. The crude solid was triturated with CHCl3 (10 mL) to afford the product as an off-white solid (0.25 g, 15%).

Workup

  1. temperatureat reflux for 72 h
  2. washthe solution was washed with 5% aqueous hydrochloric acid (25 mL), saturated aqueous sodium bicarbonate (25 mL), and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to an orange solid
  5. customThe crude solid was triturated with CHCl3 (10 mL)

Sources & evidence

ORD record
ord-b42276f9e4ed448c848f367b27cd9658
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

Loading…