Triethylamine → Methyl 3-(4-chlorobenzyloxyaminocarbonyl)-2,4-dichlorobenzoate

HRID 1368827Notes

Reaction equation

HRID 1368827 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.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([CH2:22][O:23][NH2:24])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([CH2:22][O:23][NH:24][C:2]([C:4]2[C:5]([Cl:15])=[C:6]([CH:11]=[CH:12][C:13]=2[Cl:14])[C:7]([O:9][CH3:10])=[O:8])=[O:3])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 217573Hydroxylamine, O-((4-chlorophenyl)methyl)-, hydrochloride (1:1)HCID 18517406Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

Product 1

HCID 18517404Methyl 3-(4-chlorobenzyloxyaminocarbonyl)-2,4-dichlorobenzoateYield 122.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At about 30° C., 10.70 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 50 ml of methylene chloride were slowly added dropwise to a solution of 7.76 g (0.04 mol) of O-(4-chlorobenzyl)hydroxylamine hydrochloride and 4.05 g (0.04 mol) of triethylamine in 200 ml of methylene chloride. After stirring for 12 hours at room temperature, the reaction mixture was washed with dilute phosphoric acid, dried and concentrated. Trituration of the residue with diethyl ether gave 19.00 g of methyl 3-(4-chlorobenzyloxyaminocarbonyl)-2,4-dichlorobenzoate.

Workup

  1. washthe reaction mixture was washed with dilute phosphoric acid
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ed15289d428047f8ab9e35d5e17a42d7
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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