Sodium Hydroxide → HCID 14621097, compound

HRID 1607199Notes

Reaction equation

HRID 1607199 reaction equation
C([NH:4][C:5]1[C:18]([F:19])=[CH:17][C:8]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:7]([F:20])[CH:6]=1)(=O)C.[OH-].[Na+]>CCO>[NH2:4][C:5]1[C:18]([F:19])=[CH:17][C:8]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[C:7]([F:20])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14621095HCID 14621095, compound

Product 1

HCID 14621097HCID 14621097, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture consisting of 3.6 g of 4-acetamido-α-[(tert-butylamino)methyl]-2,5-difluorobenzyl alcohol, 36 mL of EtOH and 36 mL of 10% aqueous NaOH is heated at reflux under N2 for 4 h. The EtOH is evaporated in vacuo and the residue is extracted with 4×60 mL of CH2Cl2. The combined organic extracts are washed with 25 mL of H2O, dried with anhydrous Na2SO4 and evaporated in vacuo to furnish the title compound which is crystallized from CH3CN/hexane, 2.77 g (90% yield), m.p. 115°-116° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2 for 4 h
  3. customThe EtOH is evaporated in vacuo
  4. extractionthe residue is extracted with 4×60 mL of CH2Cl2
  5. washThe combined organic extracts are washed with 25 mL of H2O
  6. dry with materialdried with anhydrous Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c22791eac1043a082b8798fd5d33e74
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

Loading…