Ammonium Hydroxide → HCID 11035745, compound

HRID 1857997Notes

Reaction equation

HRID 1857997 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:20](Cl)(=[O:22])=[O:21])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.[OH-].[NH4+:27]>O1CCOCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:20]([NH2:27])(=[O:22])=[O:21])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10872568HCID 10872568, compound

Product 1

HCID 11035745HCID 11035745, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(4-fluorobenzoyl)-6-methoxy-2-naphthalenesulfonyl chloride (5.39 g, 14.2 mmol), [prepared as described in step 2 above], in dioxane (100 ml), was cooled in an ice bath under nitrogen, and concentrated ammonium hydroxide (20 ml) was added dropwise. After 1 h, the dioxane was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 20-60% ethyl acetate/hexane) and then recrystallized from ethyl acetatelhexane to afford 2.7 g of 5-(4-fluorobenzoyl)-6-methoxy-2-naphthalenesulfonamide as white crystals.

Workup

  1. customthe dioxane was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (gradient elution, 20-60% ethyl acetate/hexane)
  8. customrecrystallized from ethyl acetatelhexane

Sources & evidence

ORD record
ord-abaa6772b5234e7ea83ee2ee6bf74fa2
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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