N,O-Dimethylhydroxylamine → N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide

HRID 924655Notes

Reaction equation

HRID 924655 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.[CH3:10][O:11][NH:12][CH3:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:10][O:11][N:12]([CH3:13])[C:7](=[O:9])[CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 234043-Thiophenacetic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11423995N-methoxy-N-methyl-2-(thiophen-3-yl)acetamideYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(thiophen-3-yl)acetic acid (2.0 g, 14.1 mmol), O,N-dimethylhydroxylamine (1.68 g, 16.9 mmol), EDCI (2.95 g, 15.5 mmol), HOBT (2.15 g, 15.5 mmol), and TEA (3.7 mL, 31 mmol) in anhydrous DCM (50 mL) was stirred at room temperature under nitrogen for two hours. The reaction mixture was diluted with CH2Cl2, and the organic layer was washed with aqueous HCl solution (0.5 mol/L, 30 mL×2), saturated NaHCO3 (30 mL×2) and brine(30 mL), dried over Na2SO4, filtered, and concentrated to give the crude N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (2.0 g, yield 76.6%).

Workup

  1. washthe organic layer was washed with aqueous HCl solution (0.5 mol/L, 30 mL×2), saturated NaHCO3 (30 mL×2) and brine(30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-03abfe3442b3403da377e9ce034b30ed
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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