Water → HCID 117806247, compound

HRID 1425911Notes

Reaction equation

HRID 1425911 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:13])(=[O:12])=[O:11])([O-:3])=[O:2].[C:14](=[O:17])([O-])[O-].[Cs+].[Cs+].[CH2:20]([C@@H:22]1[O:24][CH2:23]1)Cl.O.[C:26](#N)[CH3:27]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:26][C@@H:27]1[CH2:14][O:17]1)[CH2:20][C@@H:22]1[CH2:23][O:24]1)(=[O:11])=[O:12])([O-:3])=[O:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 1385102-NitrobenzenesulfonamideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 117806247HCID 117806247, compoundYield 32%

Procedure

To a solution of 2-nitrobenzenesulfonamide (XXX) (1 g, 4.95 mmol) in acetonitrile (1.5 mL) was added cesium carbonate (3.56 g, 10.93 mmol) followed by (R)-(−)-epichlorohydrin (XXXI) (1.6 mL, 20.4 mmol). This reaction mixture was refluxed for 16 hours. 100 mL of water was added to the cooled solution followed by extraction with EtOAc (3×75 mL) The organic layer was dried over sodium sulfate, the solvent removed under vacuum and the residue purified by automated silica gel chromatography using hexanes/EtOAc 0→100% to give 2-nitro-N,N-bis((R)-oxiran-2-ylmethyl)benzenesulfonamide (XXXII) (0.48 g, 1.5 mmol, 32% yield). 1H NMR (DMSO-d6) δ ppm 8.08 (d, J=7.8, 1H), 8.00 (d, J=7.8, 1H), 7.91 (t, J=7.6, 1H), 7.84 (t, J=7.6, 1H), 3.64 (ABq, J=4.0, 15.4, 2H), 3.38 (dd, J=3.6, 6.2, 2H), 3.12-3.08 (m, 2H), 2.75 (t, J=4.3, 2H), 2.59 (dd, J=2.6, 4.9, 2H), 2.50 (p, J=1.72, 2H). ESIMS found for C12H14N2O6S m/z 314.9 (M+H).

Workup

  1. temperatureThis reaction mixture was refluxed for 16 hours
  2. extractionfollowed by extraction with EtOAc (3×75 mL) The organic layer
  3. dry with materialwas dried over sodium sulfate
  4. customthe solvent removed under vacuum
  5. customthe residue purified by automated silica gel chromatography

Sources & evidence

ORD record
ord-abbdc653948c47f3aca823ad4d55a410
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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