Hydrochloric Acid → 2-Thiophenesulfonamide, 5-(2-aminoethyl)-, hydrochloride (1:1)

HRID 978465Notes

Reaction equation

HRID 978465 reaction equation
CN.[S:3]([C:7]1[S:11][C:10]([CH2:12][CH2:13][N:14]2C(=O)C3=CC=CC=C3C2=O)=[CH:9][CH:8]=1)(=[O:6])(=[O:5])[NH2:4].[ClH:25]>C(O)C>[ClH:25].[NH2:14][CH2:13][CH2:12][C:10]1[S:11][C:7]([S:3]([NH2:4])(=[O:6])=[O:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 13851237HCID 13851237, compound

Product 1

HCID 202032982-Thiophenesulfonamide, 5-(2-aminoethyl)-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of methylamine (9 g, 0.33 mol) in ethanol (40 ml), cooled in an ice bath, was added N-(2-(5-sulfamoyl-2-thienyl)ethyl)phthalimide (3.2 g, 9.5 mmol). After stirring for 20-25 hours, the precipitated by-product was removed by filtration. The filtrate was concentrated and diethyl ether was added to precipitate remaining by-product. This was collected on a filter. The filtrate was concentrated to dryness to give the product free base as an oil. This oil was dissolved in ethanol and 6N ethanolic HCl was slowly added as the product precipitated. The salt was twice recrystallized by dissolution in methanol and careful dilution with diethyl ether to give 1.3 g, m.p. 222°-224° C.

Workup

  1. customthe precipitated by-product was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. additiondiethyl ether was added
  4. customto precipitate
  5. customThis was collected on a filter
  6. concentrationThe filtrate was concentrated to dryness
  7. customto give the product free base as an oil
  8. customprecipitated
  9. customThe salt was twice recrystallized by dissolution in methanol
  10. customcareful dilution with diethyl ether to give 1.3 g, m.p. 222°-224° C.

Sources & evidence

ORD record
ord-8be99709706a4b0d8416e002dcd92718
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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