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

HRID 377550Notes

Reaction equation

HRID 377550 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

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

Workup

  1. washit was washed with dilute phosphoric acid
  2. customdried
  3. concentrationconcentrated
  4. extractionAfter the residue had been extracted
  5. stirringwith stirring with diethyl ether

Sources & evidence

ORD record
ord-4a42665bebbd4b59ba96a585c03dc419
Source dataset
uspto-grants-2000_02
Patent number
US06028035

Reaction notes

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