Triethylamine → N-methoxy-N-methyl-2-(3-methylphenyl)acetamide

HRID 924926Notes

Reaction equation

HRID 924926 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.Cl.[CH3:13][NH:14][O:15][CH3:16].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl>[CH3:16][O:15][N:14]([CH3:13])[C:8](=[O:9])[CH2:7][C:3]1[CH:2]=[C:1]([CH3:11])[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12121m-Tolylacetic acid2×HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 62873680N-methoxy-N-methyl-2-(3-methylphenyl)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-m-tolylacetic acid (1 g, 6.7 mmol), N,O-dimethylhydroxylamine hydrochloride (654 mg, 6.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.28 g, 6.7 mmol), hydroxybenzotriazole (910 mg, 6.7 mmol) and triethylamine (3.38 g, 33.5 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. When TLC indicated that 2-m-tolylacetic acid was consumed, the reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=10:1) to afford N-methoxy-N-methyl-2-m-tolylacetamide (900 mg, yield 70%).

Workup

  1. customwas consumed
  2. additionthe reaction mixture was diluted with water (30 mL)
  3. extractionextracted with EtOAc (30 mL×3)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-9fe7872192d14802a22f40f1bd99a765
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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