2-Methoxyethylamine → 2-Amino-5-(4-[2-methoxyethyl]aminophenylsulfonyloxy)nitrobenzene

HRID 1823762Notes

Reaction equation

HRID 1823762 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[CH3:22][O:23][CH2:24][CH2:25][NH2:26]>O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:26][CH2:25][CH2:24][O:23][CH3:22])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 120188434-Amino-3-nitrophenyl 4-fluorobenzenesulfonate

Product 1

HCID 120188472-Amino-5-(4-[2-methoxyethyl]aminophenylsulfonyloxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

15.6 g of 2-amino-5-(4-fluorophenylsulfonyloxy)nitrobenzene were combined with 35 ml methoxyethylamine in 100 ml dioxane in a round bottom flask. The reaction mixture was heated to reflux for 8 hours and then cooled to 40° C. and extracted two times with 250 ml water. Concentrate was solubilized with ethyl acetate and extracted with 2N aqueous HCl and water, the organic phase was then dried under reduced pressure, yielding 19.2 g of 2-amino-5-(4-[2-methoxyethyl]aminophenylsulfonyloxy)nitrobenzene (melting point 105° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 hours
  3. extractionextracted two times with 250 ml water
  4. concentrationConcentrate
  5. extractionextracted with 2N aqueous HCl and water
  6. customthe organic phase was then dried under reduced pressure

Sources & evidence

ORD record
ord-9c2c1c3f2c8a48109c5a6af8e6185440
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

Loading…