Sodium Hydroxide → HCID 21930289, compound

HRID 1243654Notes

Reaction equation

HRID 1243654 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=2)(=[O:15])=[O:14])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21930287HCID 21930287, compound

Product 1

HCID 21930289HCID 21930289, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-bromo-2-(4-trifluoromethoxy-benzenesulfonylamino)benzoate (0.854 g, 0.019 mmol) was dissolved in a mixture of tetrahydrofuran (20 mL)/water (10 mL). A solution of sodium hydroxide (50%, 5 mL) was added and the mixture was heated to reflux for 2–3 hours. The tetrahydrofuran was removed by rotary evaporation and the mixture was acidified with aqueous HCl (2 M). The mixture was extracted with ethyl acetate (20 mL). The organic solvent was removed to dryness. The residue was dried azeotropically by dissolution in ethyl acetate followed by evaporation (3×15 mL). This provided an oil, which was triturated in hexane (20 mL) until a solid formed. The solid was collected by filtration and dried in a vacuum oven at 40° C. Recovery=0.691 g (83% yield). M/Z of (M−H)−=432, 1H NMR (DMSO) δ=7.42–7.48 (1H), 7.55–7.6 (2H), 7.74–7.8 (1H), 7.92–8.0 (3H), 11,2 (br, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2–3 hours
  3. customThe tetrahydrofuran was removed by rotary evaporation
  4. extractionThe mixture was extracted with ethyl acetate (20 mL)
  5. customThe organic solvent was removed to dryness
  6. dry with materialThe residue was dried azeotropically by dissolution in ethyl acetate
  7. customfollowed by evaporation (3×15 mL)
  8. customThis provided an oil, which
  9. customwas triturated in hexane (20 mL) until a solid
  10. customformed
  11. filtrationThe solid was collected by filtration
  12. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-efc92a2c0a28487c9e9d6c6f6ccac661
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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