4-Chloro-3-nitrobenzenesulfonamide → HCID 67169936, compound

HRID 1520595Notes

Reaction equation

HRID 1520595 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[F:16][C:17]([F:27])([F:26])[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1.C(N(CC)CC)C.O1CCOCC1>O>[N+:12]([C:3]1[CH:4]=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:17]([F:27])([F:16])[F:26])[CH2:20][CH2:21]1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 178400021-(2,2,2-Trifluoroethyl)piperidin-4-amine hydrochloride

Product 1

HCID 67169936HCID 67169936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-chloro-3-nitrobenzenesulfonamide (1.300 g), 1-(2,2,2-trifluoroethyl)piperidin-4-amine hydrochloride (1.201 g), and triethylamine (2.30 mL) were added to 1,4-dioxane (50 mL) and water (5 mL) and heated at 90° C. for 16 hours. The solution was concentrated on vacuum and purified by flash column chromatography on silica gel with ethyl acetate increasing to 5% methanol in ethyl acetate.

Workup

  1. concentrationThe solution was concentrated on vacuum
  2. custompurified by flash column chromatography on silica gel with ethyl acetate increasing to 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-d7b895ab6f3a4256bbe01fa96c7cefa0
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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