Hydrochloric Acid → 2-(Phenylsulfonyl)ethanamine hydrochloride

HRID 4199Notes

Reaction equation

HRID 4199 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 hydrochlorideYield 40.5%

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 5% sodium hydroxide. 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, m.p. 151°-154° C. in 40.5% yield.

Workup

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

Sources & evidence

ORD record
ord-ff66ca3284074b0b8a71d6f999b087a9
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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