2-(Dimethylamino)ethanol → HCID 67448006, compound

HRID 1505215Notes

Reaction equation

HRID 1505215 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].[H-].[Na+].F[C:10]1[CH: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[CH:17]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 67448006HCID 67448006, compound

Conditions

Temperature
60 °C

Procedure

To N,N-dimethylaminoethanol (15 mL) cooled at 0° C. was added NaH 60% (1.15 g, 4 mol eq) and then 2-fluoro-4-trifluoromethyl-benzonitrile (1 mL, 7.18 mmol). The mixture was heated at 60° C. for 4 h then the solvent was removed at reduced pressure and water was added to the residue. The aqueous phase was extracted with EtOAc (3×30 mL), the organic phases were dried over sodium sulfate and evaporated to dryness to give 26b as pale yellow oil (2.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 1.21 (s, 3H), 1.31 (s, 3H), 2.21 (t, 2H, J=8), 2.48 (t, 2H, J=8), 6.54 (dd, 1H, J=2), 6.82 (m, 2H).

Workup

  1. customthe solvent was removed at reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with EtOAc (3×30 mL)
  4. dry with materialthe organic phases were dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-61df209878564979916d89af61bbc728
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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