Tetrabutylammonium Fluoride → 2-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide

HRID 1259044Notes

Reaction equation

HRID 1259044 reaction equation
[Si]([O:18][CH2:19][CH2:20][NH:21][S:22]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[Cl:34])(=[O:24])=[O:23])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:34][C:26]1[CH:27]=[CH:28][C:29]([N+:31]([O-:33])=[O:32])=[CH:30][C:25]=1[S:22]([NH:21][CH2:20][CH2:19][OH:18])(=[O:24])=[O:23]

Participants

7

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 66690588n-[2-(Tert-butyldiphenylsilanyloxy)-ethyl]-2-chloro-5-nitro-benzenesulfonamide

Product 1

HCID 145740892-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The crude N-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-2-chloro-5-nitro-benzenesulfonamide obtained above (theoretical 8.09 g) was dissolved in tetrahydrofuran (50 ml) and a 1M solution of tetrabutlyammonium fluoride in tetrahydrofuran (17.2 ml, 17.2 mmol) was added in one portion. The reaction was stirred at room temperature for 2 h then diluted with ethyl acetate (30 ml) and brine (30 ml), the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by column chromatography using hexane: ethyl acetate as eluent to afford the named product (3.44 g, 79% over 2 steps); Rf (ethyl acetate:hexane 1:1) 0.11, LCMS Rt=2.85 min, m/z (ES−) 279 (M−H).

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe reaction was purified by column chromatography
  5. customethyl acetate as eluent to afford the named product (3.44 g, 79% over 2 steps)

Sources & evidence

ORD record
ord-0d762b250d2943879dccfb677f792a28
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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