Water → HCID 69286979, compound

HRID 2224394Notes

Reaction equation

HRID 2224394 reaction equation
[CH2:1]([NH2:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].C(N(CC)CC)C.O>O1CCOCC1>[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 79882Neopentylamine

Product 1

HCID 69286979HCID 69286979, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of neopentylamine (0.86 g ml, 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 17 h, poured into water (100 ml) and extracted with dichloromethane (3×75 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 ethyl acetate/hexane to yield 3-nitro-N-(2,2-dimethyl-propyl)-benzenesulfonamide (2.14 g, 87%) as a white solid. MS (ISP) 271.1 [(M−H)−]; mp 117° C.

Workup

  1. extractionextracted with dichloromethane (3×75 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 ethyl acetate/hexane

Sources & evidence

ORD record
ord-69ef5745001b45bc857f0ae8c120944c
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

Loading…