Ethanol → HCID 22590155, compound

HRID 23611Notes

Reaction equation

HRID 23611 reaction equation
[F:1][C:2]1[CH:3]=C([CH:7]=[C:8]([F:19])[C:9]=1[N:10]([CH2:15][CH:16]([OH:18])[CH3:17])[CH2:11][CH:12]([OH:14])[CH3:13])C#N.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>>[F:1][C:2]1[CH:3]=[C:23]([CH:7]=[C:8]([F:19])[C:9]=1[N:10]([CH2:15][CH:16]([OH:18])[CH3:17])[CH2:11][CH:12]([OH:14])[CH3:13])[C:22]([OH:20])=[O:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22590143HCID 22590143, compound

Product 1

HCID 22590155HCID 22590155, compound

Procedure

A solution of the 3,5-difluoro-4-[bis(2-hydroxypropyl)amino]benzonitrile and NaOH (8 g, 0.2 mol) in aqueous ethanol (100 ml, 50%) was refluxed for 2.5 hours. The solution was partitioned between EtOAc (1.2 1) and HCl (500 ml, 0.4 M), the aqueous layer washed with EtOAc (3×240 ml), the combined organic layers dried (MgSO4) and evaporated to dryness. The residue was chromatographed using CH2Cl2-EtOH-ACOH as eluent.

Workup

  1. customThe solution was partitioned between EtOAc (1.2 1) and HCl (500 ml, 0.4 M)
  2. washthe aqueous layer washed with EtOAc (3×240 ml)
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-66ceef3ec995441e96eafebd7fc20035
Source dataset
uspto-grants-2005_02
Patent number
US06852755B1

Reaction notes

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