Triethylamine → HCID 86757554, compound

HRID 382858Notes

Reaction equation

HRID 382858 reaction equation
Cl[C:2]([C:4]1[C:5](Cl)=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([O:9][CH3:10])=[O:8])=[O:3].[ClH:16].[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:12]2[CH:13]([Cl:14])[C:4](=[C:2]=[O:3])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:11]=2[Cl:16])=[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 86757554HCID 86757554, compoundYield 122.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.70 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichloro-benzoate in 50 ml of methylene chloride were slowly added dropwise at approximately 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 by stirring with diethyl ether, 19.00 g of methyl 3-(4-chlorobenzyloxy)amino-carbonyl-2,4-dichlorobenzoate were obtained.

Workup

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

Sources & evidence

ORD record
ord-b9663db196ac441d97c40a1e395e4d48
Source dataset
uspto-grants-2001_10
Patent number
US06310245B1

Reaction notes

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