Hydrochloric Acid → 4-[N-(2,3-Epoxypropyl)sulphamoyl]nitrobenzene

HRID 1071945Notes

Reaction equation

HRID 1071945 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Br.Cl>O>[O:20]1[CH2:19][CH:18]1[CH2:16][NH:13][S:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 227844-Nitrobenzenesulfonamide

Product 1

HCID 223906444-[N-(2,3-Epoxypropyl)sulphamoyl]nitrobenzeneYield 32.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Nitrobenzene sulphonamide (6.06 g, 30 mmol) was added portionwise to a solution of sodium hydroxide (1.32 g, 33 mmol) in water (60 ml) at room temperature. Epibromohydrin (4.5 g, 33 mmol) was added quickly dropwise and the solution stirred at room temperature for 24 hours. The mixture was acidified to pH 1 with 2M hydrochloric acid and extracted with DCM (2×30 ml). The combined organic extracts were dried with sodium sulphate, filtered and the volatiles removed by evaporation. The resulting yellow oil was purified by chromatography on silica eluting with DCM/methanol (100:0) increasing in polarity to (99:1) to give the title compound as a pale yellow solid (2.5 g, 32%); NMR (CDCl3) 2.65 (m, 1H), 2.80 (t, 1H), 3.10 (m, 2H), 3.50 (m, 1H), 5.08 (brs, 1H), 8.08 (d, 2H), 8.38 (d, 2H); m/z: 257.

Workup

  1. extractionextracted with DCM (2×30 ml)
  2. dry with materialThe combined organic extracts were dried with sodium sulphate
  3. filtrationfiltered
  4. customthe volatiles removed by evaporation
  5. customThe resulting yellow oil was purified by chromatography on silica eluting with DCM/methanol (100:0)
  6. temperatureincreasing in polarity to (99:1)

Sources & evidence

ORD record
ord-24abb192926a4a6a81f31c217b80bd3c
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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