Hydrochloric Acid → 2'-[2-(Isopropylamino)ethoxy]-5'-nitromethanesulfonanilide

HRID 379713Notes

Reaction equation

HRID 379713 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].F[C:15]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:16]=1[NH:17][S:18]([CH3:21])(=[O:20])=[O:19].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH:1]([NH:4][CH2:5][CH2:6][O:7][C:15]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:16]=1[NH:17][S:18]([CH3:21])(=[O:19])=[O:20])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79942-(Isopropylamino)ethanolHCID 4416401N-(2-fluoro-5-nitrophenyl)methanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 183682892'-[2-(Isopropylamino)ethoxy]-5'-nitromethanesulfonanilideYield 88.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(Isopropylamino)ethanol (24,0 g) solution in dimethylformamide (70 ml) was added with potassium tert-butoxide (21.9 g) in an ice bathing. After being stirred for 1 hour at room temperature, the reaction mixture was cooled down to 5° C. and added drop-wise with 2′-fluoro-5′-nitromethanesulfonanilide (21.8 g) in dimethylformamide (30 ml). After being stirred for 3 hours at room temperature, the reaction mixture was added into ethyl acetate (500 ml) and solids formed were collected by filtration and washed with ethyl acetate (100 ml). Solids obtained were dissolved into water (200 ml) and the solution was adjusted to pH=7 with 2N HCl . Resultant crystals were collected by filtration, washed with water, and dried under vacuum to obtain 2′-[2-(isopropylamino)ethoxy]-5′-nitromethanesulfonanilide (26.1 g) as white crystal.

Workup

  1. temperaturethe reaction mixture was cooled down to 5° C.
  2. stirringAfter being stirred for 3 hours at room temperature
  3. customformed
  4. filtrationwere collected by filtration
  5. washwashed with ethyl acetate (100 ml)
  6. customSolids obtained
  7. filtrationResultant crystals were collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-986b22ad33be4b148ecbe07641450da2
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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