Ethanol → N-(3-aminopropyl)-N-isopropyl-2-nitrobenzenesulfonamide

HRID 1893498Notes

Reaction equation

HRID 1893498 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][N:15]([CH:28]([CH3:30])[CH3:29])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17].O.NN.C(O)C>C(OCC)C>[NH2:3][CH2:12][CH2:13][CH2:14][N:15]([CH:28]([CH3:30])[CH3:29])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 66880021N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N-isopropyl-2-nitrobenzenesulfonamide

Product 1

HCID 58135060N-(3-aminopropyl)-N-isopropyl-2-nitrobenzenesulfonamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The compound (8.11 g, 18.80 mmol) obtained in step B and hydrazine monohydrate (5 ml) were added to ethanol (200 ml) and the mixture was heated under reflux for 1 hr. The reaction mixture was cooled, and diluted with diethyl ether. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was dissolved in dichloromethane, and the solution was extracted with hydrochloric acid. The aqueous layer was alkalified with aqueous sodium hydroxide solution, extracted with dichloromethane, and the organic layer was dried over potassium carbonate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (5.62 g, yield 99%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. dissolutionThe obtained oil was dissolved in dichloromethane
  7. extractionthe solution was extracted with hydrochloric acid
  8. extractionextracted with dichloromethane
  9. dry with materialthe organic layer was dried over potassium carbonate
  10. filtrationThe insoluble material was filtered off
  11. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-17cf65876c5a42f59f86619b484d8e03
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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