Triethylamine → Methyl 2,4-dichloro-3-propoxyaminocarbonylbenzoate

HRID 1368826Notes

Reaction equation

HRID 1368826 reaction equation
Cl[C:2]([C:4]1[C:5]([Cl:15])=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([O:9][CH3:10])=[O:8])=[O:3].Cl.[CH2:17]([O:20][NH2:21])[CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:15][C:5]1[C:4]([C:2]([NH:21][O:20][CH2:17][CH2:18][CH3:19])=[O:3])=[C:13]([Cl:14])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12283955O-propylhydroxylamine hydrochlorideHCID 18517406Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

Product 1

HCID 18517417Methyl 2,4-dichloro-3-propoxyaminocarbonylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 30° C., 10.7 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 100 ml of methylene chloride were slowly added dropwise to a solution of 4.50 g (0.04 mol) of O-propylhydroxylamine hydrochloride and 4.05 g (0.04 mol) of triethylamine in 200 ml of methylene chloride. After stirring for 2 hours at room temperature, the reaction mixture was washed with dilute phosphoric acid, dried and concentrated. The resulting residue was chromatographed over silica gel (eluent:toluene/ethyl acetate=9/1). 11.50 g.of methyl 2,4-dichloro-3-propoxyaminocarbonylbenzoate were obtained.

Workup

  1. washthe reaction mixture was washed with dilute phosphoric acid
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting residue was chromatographed over silica gel (eluent:toluene/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-318d1f42b502454eb380d71a423efc6b
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

Loading…