2-(Dimethylamino)ethanol → HCID 67171904, compound

HRID 1630369Notes

Reaction equation

HRID 1630369 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([CH3:25])[C:17]=1[OH:26].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]O>C(OCC)(=O)C>[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([CH3:25])[C:17]=1[O:26][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 170302,6-Xylenol, 4-nitro-HCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 67171904HCID 67171904, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.4 mL of diisopropyl azodicarboxylate was added to 1.9 g of 2,6-dimethyl-4-nitrophenol and 1.71 mL of 2-dimethylaminoethanol, and stirred at room temperature for 16 hours. The reaction liquid was diluted with ethyl acetate, and the organic layer was extracted with 2 N hydrochloric acid. The aqueous layer was made basic with aqueous 2 N sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure to obtain 667 mg of the entitled compound.

Workup

  1. customThe reaction liquid
  2. extractionthe organic layer was extracted with 2 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-f70af0936c0a47929cf9487329bb2496
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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