Potassium Hydroxide → HCID 57434735, compound

HRID 1787992Notes

Reaction equation

HRID 1787992 reaction equation
[CH:1]([NH:4][CH3:5])([CH3:3])[CH3:2].[OH-].[K+].[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18])([O-:10])=[O:9]>O.C1COCC1>[CH:1]([N:4]([CH3:5])[S:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N+:8]([O-:10])=[O:9])(=[O:18])=[O:19])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 155402-Nitrobenzenesulfonyl chlorideHCID 78485N-Methylisopropylamine

Product 1

HCID 57434735HCID 57434735, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 250 mL round bottom flask was equipped with a magnetic stirrer. The flask was charged with isopropylmethylamine (0.85 g, 11.6 mmol) followed by THF (50 mL). The mixture was cooled to 0° C. by placing the flask in an ice bath. Potassium hydroxide (23.2 mmol) was dissolved in water (20 mL) and added to the flask. An addition funnel was installed and charged with 2-nitrobenzenesulfonyl chloride (11.6 mmol) in THF (40 mL). The solution was added dropwise over 20 minutes, then the ice bath was removed. TLC (dichloromethane) indicated that the reaction was complete after addition of the 2-nitro-benzenesulfonyl chloride. The reaction was concentrated under diminished pressure, water (100 mL) was added, the mixture extracted with ethyl acetate (150 mL), dried (Na2SO4), and filtered. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and loaded onto a plug of silica gel (400 g in a 600 mL sintered glass funnel), and eluted with dichloromethane. Fractions were taken (100 mL) until the product eluted, as determined by TLC. Fractions containing the product were collected, and the solvent was removed in vacuo to yield N-(isopropyl)-N-(methyl)-2-nitrobenzenesulfonamide as a pale yellow oil. 3.08 g, (88%). 1H-NMR (CDCl3): δ 1.12-1.14 (d, 6H, J=6.7 Hz); 2.81 (s, 3H); 4.18-4.24 (m, 1H, J=6.7 Hz); 7.61-7.69 (m, 3H); 8.03-8.06 (m, 1H).

Workup

  1. customA 250 mL round bottom flask was equipped with a magnetic stirrer
  2. additionadded to the flask
  3. customAn addition funnel was installed
  4. additionThe solution was added dropwise over 20 minutes
  5. customthe ice bath was removed
  6. additionafter addition of the 2-nitro-benzenesulfonyl chloride
  7. concentrationThe reaction was concentrated under diminished pressure, water (100 mL)
  8. additionwas added
  9. extractionthe mixture extracted with ethyl acetate (150 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customThe solvent was removed under reduced pressure
  13. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  14. washeluted with dichloromethane
  15. washeluted
  16. additionFractions containing the product
  17. customwere collected
  18. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ec8005e4ee6544279e14df239f978c4e
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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