Pyridine → 4-tert-butyl-N-[4-chloro-2-(5-isopropoxymethyl-[1,3,4]oxadiazol-2-yl)-phenyl]-benzenesulfonamide

HRID 448106

Reaction equation

HRID 448106 reaction equation
S(Cl)(Cl)=O.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[C:26]([NH:28][NH:29][C:30](=[O:36])[CH2:31][O:32][CH:33]([CH3:35])[CH3:34])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].N1C=CC=CC=1>C(OCC)C>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[C:26]2[O:36][C:30]([CH2:31][O:32][CH:33]([CH3:35])[CH3:34])=[N:29][N:28]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:6])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 669056074-tert-butyl-N-{4-chloro-2-[N'-(2-isopropoxy-acetyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

Product 1

HCID 669052774-tert-butyl-N-[4-chloro-2-(5-isopropoxymethyl-[1,3,4]oxadiazol-2-yl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride was added to a solution of 4-tert-butyl-N-{4-chloro-2-[N′-(2-isopropoxy-acetyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide (150 mg, 0.312 mmol) and pyridine (66 μL, 0.811 mmol) in diethyl ether (3 mL). The resultant solution was stirred for 18 h at room temperature followed by removal of the volatiles in vacuo. 2 mL toluene was subsequently added and the reaction was heated at reflux for 5 h. The resultant solution was concentrated at reduced pressure and the residue purified via flash column chromatography (0-50% ethyl acetate in hexane) to afford 4-tert-butyl-N-[4-chloro-2-(5-isopropoxymethyl-[1,3,4]oxadiazol-2-yl)-phenyl]-benzenesulfonamide as a white solid.

Workup

  1. customfollowed by removal of the volatiles in vacuo
  2. addition2 mL toluene was subsequently added
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 5 h
  5. concentrationThe resultant solution was concentrated at reduced pressure
  6. customthe residue purified via flash column chromatography (0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-410361b1d2ca4cffae6567c708c06195
Source dataset
uspto-grants-2013_07
Patent number
US08481579B2

Linked notes

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