Acetic Acid → Hydrochloric Acid

HRID 1438104Notes

Reaction equation

HRID 1438104 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19](=[O:22])(=[O:21])[NH2:20])[CH:14]=1)=O)(C)(C)C.CC(O)=O.[ClH:27].O1CCOCC1>CCO.[Pt]>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:14]=[C:15]([S:19]([NH2:20])(=[O:21])=[O:22])[CH:16]=[CH:17][CH:18]=1.[ClH:27]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 204431481,4-Dioxane hydrochlorideHCID 579428152-(3-Sulfamoyl-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 579427353-Pyrrolidin-2-yl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3B (290 mg, 0.9 mmol) was hydrogenated in EtOH (9.0 mL) and HOAc (0.15 mL) with Pt/C (5% wt, 100 mg) using a H2 balloon for 2 days. After filtration and evaporation of solvent, the crude product was stirred in EtOAc (1.0 mL) and 4.0 N HCl/dioxane (4.3 mL, 18 eq) at rt for 1.0 h. After removal of solvent, 3C was obtained as HCl salt. 1H NMR (400 MHz, Methanol-d4) δ ppm 2.26 (m, 3H) 2.55 (m, 1H) 3.49 (m, 2H) 4.74 (dd, J=10.11, 6.59 Hz, 1H) 7.66 (t, J=7.69 Hz, 1H) 7.74 (m, 1H) 7.97 (d, J=7.91 Hz, 1H) 8.04 (s, 1H).

Workup

  1. customfor 2 days
  2. filtrationAfter filtration and evaporation of solvent
  3. customAfter removal of solvent

Sources & evidence

ORD record
ord-746267a608724c8fadab1f50a424bd47
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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