2-(Dimethylamino)ethanol → HCID 12992938, compound

HRID 844239Notes

Reaction equation

HRID 844239 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7]O)[CH3:5].[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][N:16]2S(C)(=O)=O)=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][N:16]2[CH2:7][CH2:6][N:4]([CH3:5])[CH3:3])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 18007495HCID 18007495, compound

Product 1

HCID 12992938HCID 12992938, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a powdered suspension of NaH (55 mg, 4.8 mmol) in toluene (4 mL) was added 2-(N,N-dimethylamino)ethanol (321 mg, 3.6 mmol). The mixture was stirred for 10 minutes, after which compound (i), above, (751 mg, 2.4 mmol) was added and the mixture refluxed 16 h. The mixture was allowed to cool to room temperature and then diluted with CH2Cl2. The organic extract was washed with water and brine and dried over anhydrous Na2SO4. The crude residue was purified by flash chromatography to give the title product as a white solid (390 mg, 61% yield).

Workup

  1. temperaturethe mixture refluxed 16 h
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e2d46347151a429fa58b45c9b3d5be71
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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