2-(Dimethylamino)ethanol → HCID 67450105, compound

HRID 1505214Notes

Reaction equation

HRID 1505214 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].[H-].[Na+].Cl[C:10]1[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][C:10]1[C:11]([C:12]#[N:13])=[CH:14][CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[N:17]=1

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrile

Product 1

HCID 67450105HCID 67450105, compoundYield 92%

Conditions

Temperature
65 °C

Procedure

To N,N-dimethylaminoethanol (25 mL) at 0° C. was added in small portion NaH 60% (4 mol eq, 0.465 g, 11.62 mmol) and after 10 min 2-chloro-6-trifluoromethyl-nicotinonitrile (0.6 g, 2.90 mmol) was slowly added. The mixture was heated at 65° C. for 4 h. Then the solvent was removed at reduced pressure, water was added and the aqueous phase was extracted with EtOAc (3×30 mL). The recombined organic phases were washed with brine, anhydrified over Na2SO4 and evaporated at reduced pressure to obtain a pale yellow oil (0.69 g, 2.66 mmol, 92% Yield) used for the next step of reaction without further purification.

Workup

  1. customThen the solvent was removed at reduced pressure, water
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  4. washThe recombined organic phases were washed with brine
  5. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-1617187ed7444e7a83d3866dc0fcd1dc
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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