N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2,4-dinitrobenzenesulfonamide → 2,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

HRID 1256177Notes

Reaction equation

HRID 1256177 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=3[N+:24]([O-])=O)(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1>[Ni]>[NH2:24][C:16]1[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:15]=1[S:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)(=[O:13])=[O:14]

Participants

3

Reactant 1

HCID 86655244N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2,4-dinitrobenzenesulfonamide

Product 1

HCID 671737422,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2,4-dinitrobenzenesulfonamide (0.43 g, 1.14 mmol) was added Raney-Ni (100 mg), following by degas and replacement of air with H2. The reaction mixture was hydrogenated at room temperature for 2 hours. Once the reaction was completed (LC/MS), the mixture was filtered through Celite®. The filtrate was concentrated in vacuo to give a gummy material. The crude product was recrystallized in MeOH to give the title compound as an off-white solid (0.32 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.15 (s, 1H), 7.41 (s, 1H), 7.10˜7.18 (m, 3H), 5.72˜5.73 (m, 2H), 5.60 (s, 1H), 5.52 (s, 2H), 4.84 (s, 2H); MS (ESI) m/z=318 (M−1, negative); HPLC purity: 99.6% (MaxPlot 200-400 nm), 99.3% (220 nm).

Workup

  1. customby degas
  2. filtrationthe mixture was filtered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a gummy material
  5. customThe crude product was recrystallized in MeOH

Sources & evidence

ORD record
ord-9bcbc044f5cd4634b62de9a73c659061
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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