Oxalyl chloride → 4-tert-butyl-N-{4-chloro-2-[N'-(2-isopropoxy-acetyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

HRID 448105

Reaktionsgleichung

Reaktionsgleichung von HRID 448105
C(Cl)(=O)C(Cl)=O.[CH:7]([O:10][CH2:11][C:12]([OH:14])=O)([CH3:9])[CH3:8].[C:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[C:36]([NH:38][NH2:39])=[O:37])(=[O:27])=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>ClCCl.C1COCC1>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[C:36]([NH:38][NH:39][C:12](=[O:14])[CH2:11][O:10][CH:7]([CH3:8])[CH3:9])=[O:37])(=[O:26])=[O:27])=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

6

Edukt 3

HCID 65578Oxalyl chlorideHCID 5172132-(Propan-2-yloxy)acetic acidHCID 593029884-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)benzenesulfonamide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.19 mL, 2.20 mmol) was added to a solution of isopropoxyacetic acid (200 mg, 1.69 mmol) in dichloromethane (17 mL) and stirred at room temperature for 2 hours. The reaction was concentrated and 3 mL of THF was added. The acid chloride solution was subsequently slowly added to a solution of 4-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (645 mg, 1.69 mmol) in 10 mL of THF at 0° C. After the reaction was stirred for 1 h, it was quenched with water and diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×) and dichloromethane (2×), and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude reside was purified by flash column chromatography (0-100% ethyl acetate in hexane) to yield 4-tert-butyl-N-{4-chloro-2-[N′-(2-isopropoxy-acetyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide as a yellow solid.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. addition3 mL of THF was added
  3. stirringAfter the reaction was stirred for 1 h
  4. customit was quenched with water
  5. additiondiluted with ethyl acetate
  6. extractionThe aqueous phase was extracted with ethyl acetate (3×) and dichloromethane (2×)
  7. dry with materialthe combined organic layers were dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude reside was purified by flash column chromatography (0-100% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b94f0ddb1c684bde8fdfc7a54019eb56
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481579B2

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