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

HRID 382856
Notes
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Reaction equation

HRID 382856 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][NH2:11].Cl[C:13]([C:15]1[C:16]([Cl:26])=[C:17]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:18]([O:20][CH3:21])=[O:19])=[O:14]>ClCCl>[Cl:26][C:16]1[C:15]([C:13]([NH:11][O:10][CH3:9])=[O:14])=[C:24]([Cl:25])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 18517406Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

Product 1

HCID 18517407Methyl 2,4-dichloro-3-methoxyaminocarbonylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 4.60 g (0.045 mol) of triethylamine and 3.75 g (0.045 mol) of methoxyamine hydrochloride were added to a solution of 5.35 g (0.02 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate and in 100 ml of dichloromethane. After the reaction solution had been stirred for 12 hours at room temperature, it was washed with dilute phosphoric acid, dried and concentrated. The resulting residue was extracted by stirring with diethyl ether. This gave 4.80 g of methyl 2,4-dichloro-3-(N-methoxy)aminocarbonylbenzoate.

Workup

  1. washit was washed with dilute phosphoric acid
  2. customdried
  3. concentrationconcentrated
  4. extractionThe resulting residue was extracted
  5. stirringby stirring with diethyl ether

Sources & evidence

ORD record
ord-31ac2f745f4b45608ee36a81c281f060
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06310245B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes