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

HRID 2218224Notes

Reaction equation

HRID 2218224 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[CH3:16][O:15][N:14]([CH3:13])[C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 12121m-Tolylacetic acidHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 62873680N-methoxy-N-methyl-2-(3-methylphenyl)acetamideYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-methylphenyl)acetic acid (1.0 g, 6.7 mmol) in DMF (20 mL0 were added N,O-dimethylhydroxylamine hydrochloride (0.78 g, 8.04 mmol), EDC (1.54 g, 8.04 mmol), HOBt (1.06. g, 8.04 mmol), and N,N-diisopropylethylamine (7.0 mL, 40.2 mmol). The solution was stirred at RT for 18 h then diluted with EtOAc (150 mL) and washed with HCl 1M (100 mL), water (100 mL), saturated solution of NaHCO3 (100 mL), and brine (100 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo to afford the desired amide (1.2 g, 98%) used in the next step without further purification. Rf 0.8 (EtOAc/hexanes 1/1).

Workup

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

Sources & evidence

ORD record
ord-aa60febe8528466d8118dbc21abfbadf
Source dataset
uspto-grants-2008_08
Patent number
US07410991B2

Reaction notes

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