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

HRID 1256176Notes

Reaction equation

HRID 1256176 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.[N+:12]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[S:24](Cl)(=[O:26])=[O:25])([O-:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl>[OH:10][B:7]1[C:6]2[CH:11]=[C:2]([NH:1][S:24]([C:16]3[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=3[N+:12]([O-:14])=[O:13])(=[O:25])=[O:26])[CH:3]=[CH:4][C:5]=2[CH2:9][O:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-HCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure 1: 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (4.9 g, 32.6 mmol), 2,4-dinitro-benzenesulfonyl chloride (9.8 g, 36.8 mmol), pyridine (18 mL), methylene chloride (100 ml), 0° C.-rt, 0/N. Purification: precipitation from hot H2O. The title compound was recrystallized from ethyl acetate as a light-orange solid (9.5 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.0 (s, 1H), 9.27 (s, 1H), 8.88 (d, Hz, 1H), 8.58 (dd, J=2.2, 8.6 Hz, 1H), 8.17 (d, J=8.6 Hz, 1H), 7.51 (d, Hz, 1H), 7.34 (d, J=8.3 Hz, 1H), (dd, J=1.9, 8.3 Hz, 1H), 4.91 (s, 2H); MS (ESI) m/z=378 (M−1, negative).

Workup

  1. customPurification
  2. customprecipitation from hot H2O
  3. customThe title compound was recrystallized from ethyl acetate as a light-orange solid (9.5 g)

Sources & evidence

ORD record
ord-cf321159ac294eefaa421fc7c5222ad0
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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