Sodium Hydroxide → HCID 68678011, compound

HRID 1441752Notes

Reaction equation

HRID 1441752 reaction equation
[O:1]1[CH2:6][CH2:5]OCC1.[OH-:7].[Na+].[CH3:9][N:10]([CH3:27])[CH2:11][CH2:12][N:13]([CH3:26])[C:14]1[CH:21]=[CH:20]C(C#N)=[CH:16][C:15]=1[C:22]([F:25])([F:24])[F:23]>O>[CH3:9][N:10]([CH3:27])[CH2:11][CH2:12][N:13]([CH3:26])[C:14]1[CH:21]=[CH:20][C:5]([C:6]([OH:1])=[O:7])=[CH:16][C:15]=1[C:22]([F:25])([F:24])[F:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 68676678HCID 68676678, compound

Product 1

HCID 68678011HCID 68678011, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture consisting of 25 mL dioxane, 12.5 mL water and 9.4 mL 2M aqueous sodium hydroxide solution is added to 4-[[2-(dimethylamino)ethyl]methylamino]-3-(trifluoromethyl)-benzonitrile (1.35 g, 5 mmol) and the reaction mixture shaken in for 16 hours at 95° C. After cooling, the mixture is evaporated is evaporated to dryness under reduced pressure. The resulting residue is treated with water, the pH adjusted to ˜5 with 1M hydrochloric acid and the mixture evaporated to dryness under reduced pressure. The solid residue is treated with methanol, the suspension filtered and the filtrate evaporated to yield the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is evaporated
  3. customis evaporated to dryness under reduced pressure
  4. additionThe resulting residue is treated with water
  5. customthe mixture evaporated to dryness under reduced pressure
  6. additionThe solid residue is treated with methanol
  7. filtrationthe suspension filtered
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ed7265f93fdc4a1da608b3fb32c7cb90
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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