Triethylamine → 2-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamide

HRID 924930Notes

Reaction equation

HRID 924930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:14][NH:15][O:16][CH3:17].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 798743,4-Dichlorophenylacetic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 152789332-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamideYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3,4-dichlorophenyl)acetic acid (1 g, 4.9 mmol), N,O-dimethylhydroxylamine hydrochloride (480 mg, 4.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (940 mg, 4.9 mmol), hydroxybenzotriazole (660 mg, 4.9 mmol), and triethylamine (2.5 g, 25 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layers were dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=10:1) to afford 2-(3,4-dichlorophenyl)-N-methoxy-N-methylacetamide (880 mg, yield 72.7%).

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-ddbf2c0160154c92a82feef68b033402
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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