3-Nitrobenzenesulfonyl chloride → HCID 20035222, compound

HRID 231357Notes

Reaction equation

HRID 231357 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([Cl:19])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]>O1CCCC1>[ClH:19].[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][S:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 20035222HCID 20035222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-dimethylaminoethylamine (2.2 ml, 20 mmol) in tetrahydrofuran (25 ml) was added over 30 minutes to a stirred solution of 3-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in tetrahydrofuran (50 ml) cooled in an ice bath. After addition was complete, the reaction mixture was stirred in the ice bath for 30 minutes, then at 20°-25° for 20 hours. Solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The ethyl acetate extract was washed with a saturated aqueous solution of sodium chloride, dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed on silica gel and eluted with 5% methanol-95% chloroform to give pure base. Further purification was effected by conversion to the HCl salt (1.75 g), m.p. 174.0°-76.0° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. customSolvent was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionThe ethyl acetate extract
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed on silica gel
  11. washeluted with 5% methanol-95% chloroform
  12. customto give pure base
  13. customFurther purification

Sources & evidence

ORD record
ord-68fa12bc74024d88ad1699464f863578
Source dataset
uspto-grants-1989_07
Patent number
US04845284

Reaction notes

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