Hydrochloric Acid → 2-(Phenylsulfonyl)ethanamine hydrochloride

HRID 330415Notes

Reaction equation

HRID 330415 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.[ClH:26]>C(O)C>[ClH:26].[C:1]1([S:7]([CH2:10][CH2:11][NH2:12])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 3030034N-(2-(Phenylsulfonyl)ethyl)phthalimide

Product 1

HCID 136550652-(Phenylsulfonyl)ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 32.3 g (0.102 mole) of 2-[2-(phenylsulfonyl)ethyl]-1H-isoindole-1,3-(2H)-dione and 11.8 g (0.2 mole) of 85% hydrazine hydrate in 500 ml of absolute ethanol was refluxed for 6 hr. The reaction mixture was cooled to room temperature, filtered and concentrated. The concentrate was dissolved in chloroform and extracted with a 5% sodium hydroxide solution. The chloroform layer was dried and evaporated to give a clear oil. The oil (the free base of the title compound) was reacted with ethereal hydrogen chloride. Recrystallization of the precipitated salt from methanol-diethyl ether gave white crystalline product (40.5% yield), m.p. 151°-154° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in chloroform
  4. extractionextracted with a 5% sodium hydroxide solution
  5. dry with materialThe chloroform layer was dried
  6. customevaporated
  7. customto give a clear oil

Sources & evidence

ORD record
ord-a3da49be8fb34ac4bb286658a49017f3
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

Loading…