2-Nitropropane → HCID 14622559, compound

HRID 1638710Notes

Reaction equation

HRID 1638710 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)(=[O:8])=[O:7].[Li].[N+:22]([CH:25]([CH3:27])[CH3:26])([O-:24])=[O:23]>CS(C)=O>[ClH:15].[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:25]([CH3:27])([N+:22]([O-:24])=[O:23])[CH3:26])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 3028194Lithium2×HCID 14622557HCID 14622557, compound

Product 1

HCID 14622559HCID 14622559, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N-(2-dimethylaminoethyl)-N-methyl-4-chloro-3-nitrobenzenesulfonamide base (15.65 g, 49 mmol) and the lithium salt of 2-nitropropane (4.66 g, 49 mmol) in dimethylsulfoxide (100 mL) was stirred under nitrogen at 20°-25° for 3 days. An additional 0.35 g of the lithium salt was then added and stirring continued for three days more. After pouring the reaction mixture on ice, product was extracted into a 1:1 mixture of ethyl acetate and toluene which was washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel and elution with 3% methanol-97% methylene chloride afforded 2.0 g of product. Treatment with anhydrous ethanolic hydrogen chloride and recrystallization from methanol-ethyl acetate hexane gave the hydrochloride salt, m.p. 231°-32.5° dec.

Workup

  1. additionAfter pouring the reaction mixture on ice, product
  2. extractionwas extracted into a 1:1 mixture of ethyl acetate and toluene which
  3. washwas washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash chromatography of the residue over silica gel and elution with 3% methanol-97% methylene chloride

Sources & evidence

ORD record
ord-731603d6433748a48ff16488847a9d8c
Source dataset
uspto-grants-1989_11
Patent number
US04880821

Reaction notes

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