Sodium Hydroxide → HCID 54047831, compound

HRID 1006660Notes

Reaction equation

HRID 1006660 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.BrC1C2C(C)(C)C(CS([O-])(=O)=O)(CC2)C1=O.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:25])([C:16]([C:18]1[CH:19]=[CH:20][C:21]([I:24])=[CH:22][CH:23]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131724587HCID 131724587, compound

Product 1

HCID 54047831HCID 54047831, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (g) (206.5 g, 0.27 moles) was added to methylene chloride (620 ml) and basified with 40% NaOH. The mixture was stirred for 15 minutes at room temperature and separated. The aqueous phase was re-extracted with methylene chloride (310 ml). The organic product solution was washed with water (620 ml) and concentrated to a volume of 245 ml. To the stirred and seeded concentrate at room temperature was added hexane (2450 ml) at a steady rate. The resulting slurry was granulated at 5° C. for 1 hour. Filtration afforded a white solid (117.4 g, 0.26 moles) which was characterized by 1H NMR spectroscopy.

Workup

  1. customseparated
  2. extractionThe aqueous phase was re-extracted with methylene chloride (310 ml)
  3. washThe organic product solution was washed with water (620 ml)
  4. concentrationconcentrated to a volume of 245 ml
  5. stirringTo the stirred
  6. concentrationseeded concentrate at room temperature
  7. additionwas added hexane (2450 ml) at a steady rate
  8. waitThe resulting slurry was granulated at 5° C. for 1 hour
  9. filtrationFiltration

Sources & evidence

ORD record
ord-13171dc29dc94ae081f826123b734ff9
Source dataset
uspto-grants-2004_09
Patent number
US06790957B2

Reaction notes

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