Pyridine → 2-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide

HRID 1256103Notes

Reaction equation

HRID 1256103 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.N1C=CC=CC=1.[C:18]([C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[S:29](Cl)(=[O:31])=[O:30])#[N:19]>CC#N.CN(C=O)C>[C:18]([C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[S:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1)(=[O:31])=[O:30])#[N:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 433636332-Cyano-4-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 671740652-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (16.4 g, 0.11 mol) and pyridine (10.3 g, 0.13 mol) in MeCN/DMF (400 mL/100 mL) was added 2-cyano-4-nitrobenzene-1-sulfonyl chloride (24.7 g, 0.1 mol) at 0° C., then the solution was stirred at room temperature overnight. The mixture was concentrated in vacuo, and DCM and water was added to the residue. The organic layer was dried over Na2SO4 and concentrated to give the crude product.

Workup

  1. concentrationThe mixture was concentrated in vacuo, and DCM and water
  2. additionwas added to the residue
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b229b69169d447adbfe0c0a4665dfc64
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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