Water → HCID 69288145, compound

HRID 2224397Notes

Reaction equation

HRID 2224397 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[N+:10]([C:13]1[CH:14]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].C(N(CC)CC)C.O>O1CCOCC1>[N+:10]([C:13]1[CH:14]=[C:15]([S:19]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 832754-Pyridineethanamine

Product 1

HCID 69288145HCID 69288145, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-(2-aminoethyl)-pyridine (1.21 g, 9.93 mmol) in dioxane (25 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (2.0 g, 9.02 mmol) and triethylamine (1.38 ml, 9.93 mmol). The light yellow suspension was stirred at room temperature for 6 h, poured into water (100 ml) and extracted with dichloromethane (6×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by crystallization from methanol/hexane to yield 3-nitro-N-(2-pyridine-4-yl-ethyl)-benzenesulfonamide (1.63 g, 59%) as an orange solid. MS (ISP) 306.1 [(M−H)−]; mp 153° C.

Workup

  1. extractionextracted with dichloromethane (6×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by crystallization from methanol/hexane

Sources & evidence

ORD record
ord-a61721d471d241a2a51a60e5570351aa
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

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