Hydrochloric Acid → 4-Aminocyclohexane-1-sulfonamide

HRID 1483837Notes

Reaction equation

HRID 1483837 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1.Cl>CCO>[NH2:3][CH:12]1[CH2:17][CH2:16][CH:15]([S:18]([NH2:21])(=[O:19])=[O:20])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 712276614-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonamide

Product 1

HCID 893898974-Aminocyclohexane-1-sulfonamideYield 40.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-sulfonamide (3 g, 9.7 mmol) and NH2NH2H2O (1 mL) in EtOH (15 mL) was heated at reflux for 30 min. After cooling, the pH was adjusted with diluted HCl to 5. The mixture was concentrated in vacuo. The residue was dissipated with 35% HCl (10 mL) and heating until all solid material was dissolved. Upon cooling, a crystalline material was filtered and the filtrated was concentrated to give crude 4-aminocyclohexane-1-sulfonamide (700 mg, 40%) as a yellow solid, which was used in the next step directly.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. temperatureAfter cooling
  4. concentrationThe mixture was concentrated in vacuo
  5. temperatureheating until all solid material
  6. dissolutionwas dissolved
  7. temperatureUpon cooling
  8. filtrationa crystalline material was filtered
  9. concentrationthe filtrated was concentrated

Sources & evidence

ORD record
ord-ef1803ba20484ee4ae800665696834c8
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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