Hydrochloric Acid → 2-Fluoro-5-oxiranyl-benzenesulfonamide

HRID 990600Notes

Reaction equation

HRID 990600 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:15])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1)=[O:4].[BH4-].[Na+].[OH-].[Na+].Cl>CO>[F:15][C:8]1[CH:7]=[CH:6][C:5]([CH:3]2[CH2:2][O:4]2)=[CH:10][C:9]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 118085905-(2-Bromoacetyl)-2-fluorobenzenesulphonamide

Product 1

HCID 109877122-Fluoro-5-oxiranyl-benzenesulfonamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.5 g (1.7 mmol) of 5-bromoacetyl-2-fluoro-benzenesulfonamide V in 20 mL MeOH was cooled to 0° C. NaBH4 26 mg (0.67 mmol) was added and the reaction was stirred at 0° C. for 15 min. 4 mL of 1N NaOH was added and the reaction was stirred at 0° C. for 4 hrs. The reaction was adjusted to pH 6 by addition of dilute HCl. The volatiles were evaporated and the residue dissolved in EtOAc, washed with H2O, dried over Na2SO4 and evaporated. The product was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH::9/1 to give 180 mg of VI (48%); mp 100-103° C.TLC:CH2Cl2/MeOH::9/1 single-spot material Rƒ 0.65.1H-NMR (300 MHz DMSO-D6) δ: (2.82, m, 1H), (3.14, m, 1H), (4.06, m, 1H), (7.40, t, 1H), (7.56, m, 1H), (7.66, m, 3H).

Workup

  1. stirringthe reaction was stirred at 0° C. for 4 hrs
  2. customThe volatiles were evaporated
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe product was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-7d630e878c6b4ee3b761c84695749569
Source dataset
uspto-grants-2002_10
Patent number
US06461822B2

Reaction notes

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