Pyridine → 2,3,4-Trichloro-N-[3-(1H-tetrazol-5-yl)phenyl]benzenesulfonamide

HRID 589680Notes

Reaction equation

HRID 589680 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[NH2:14][C:15]1[CH:16]=[C:17]([C:21]2[NH:25][N:24]=[N:23][N:22]=2)[CH:18]=[CH:19][CH:20]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[S:10]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[NH:25][N:24]=[N:23][N:22]=2)[CH:16]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 369042,3,4-Trichlorobenzenesulfonyl chlorideHCID 178507542HCID 178507542, compound

Product 1

HCID 1785275052,3,4-Trichloro-N-[3-(1H-tetrazol-5-yl)phenyl]benzenesulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3,4-trichlorobenzenesulfonyl chloride (15 mg, 0.055 mmol), 5-(3-aminophenyl)tetrazole (8 mg, 0.05 mmol) and dry pyridine (12 μL) in CH2Cl2 (200 μL) was stirred at room temperature over night. The solvent was evaporated and the crude product was purified by preparative HPLC (ACE C8, 5 μm 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/CH3CN) to give 13 mg (65%) of the title compound. MS (ESI+) calcd for C13H8Cl3N5O2S 402.946428, found 402.946188.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by preparative HPLC (ACE C8, 5 μm 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/CH3CN)

Sources & evidence

ORD record
ord-6cf7232f46054717b933c3d50abe3712
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

Loading…