1,2-Dichloroethane → N-methoxy-N-methyl-2-(3-methylphenyl)acetamide

HRID 1868437Notes

Reaction equation

HRID 1868437 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](O)=[O:9])[CH:2]=1.N#[N+][O-].Cl.[CH3:16][N:17](C)[OH:18].[CH2:20](Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:20][O:18][N:17]([CH3:16])[C:8](=[O:9])[CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH3:11])[CH:2]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 12121m-Tolylacetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 178485762HCID 178485762, compound

Product 1

HCID 62873680N-methoxy-N-methyl-2-(3-methylphenyl)acetamideYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of m-tolyl acetic acid (2.0 g, 0.013 mol) in DMF (20 mL) were added N2O-dimethyl hydroxylamine hydrochloride (1.6 g, 0.016 mol), EDC (3.06 g, 0.016 mol), HOAt (2.17 g, 0.016 mol), and DIPEA (11.6 mL, 0.067 mol). The resulting solution was stirred at RT for 18 h then was diluted with EtOAc (200 mL) and washed with HCl 1M (100 mL), water (100 mL), sat. sol. NaHCO3 (100 mL), and brine (100 mL). The organic phase was dried over sodium sulfate and concentrated in vacuo to afford the title intermediate (2.2 g, 88%) as colorless oil used in the next step without further purification.

Workup

  1. washwashed with HCl 1M (100 mL), water (100 mL), sat. sol. NaHCO3 (100 mL), and brine (100 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c1440632dfd4f67becf177d58f02dbc
Source dataset
uspto-grants-2009_12
Patent number
US07635713B2

Reaction notes

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