4-Methylmorpholine → benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazide

HRID 602801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602801
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:15]C(C1C=CC=CC=1)C(O)=O.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.CN1CC[O:40][CH2:39][CH2:38]1.CCN=C=NCCCN(C)C.[NH4+].[Cl-]>C1COCC1>[I:15][C:30]1[CH:35]=[CH:34][C:33]([CH2:38][C:39]([NH:14][NH:13][C:11](=[O:12])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])=[O:40])=[CH:32][CH:31]=1

Komponenten

8

Edukt 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 9943159Iodophenylacetic acidHCID 11378890Benzenesulfonyl-acetic acid hydrazide

Produkt 1

HCID 67266905benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazideAusbeute 469,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1 g (4.7 mmol) of benzenesulfonyl-acetic acid hydrazide (example 74.1) in 4 mL of THF was treated with 391 mg (4.7 mmol) of iodophenylacetic acid, 126 mg (0.93 mmol) of 1-hydroxybenzotriazole and 2.8 g (28 mmol) of N-methylmorpholine. The mixture was stirred during 15 min at 0° C., treated with 1.25 g (6.5 mmol) of EDCI and stirred during 12 hrs. The crude was treated with diluted aqueous NH4Cl and extracted twice with EtOAc. Drying of the combined organic layers over Na2SO4, filtration and evaporation gave 2 g (93%) of benzenesulfonyl-acetic acid N′-[2-(4-iodo-phenyl)-acetyl]-hydrazide as a brown oil, MS: 266 (MH+)

Aufarbeitung

  1. stirringstirred during 12 hrs
  2. extractionextracted twice with EtOAc
  3. dry with materialDrying of the combined organic layers over Na2SO4, filtration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-184aee9abcfc4afcbfcf236f9652ebda
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906546B2

Notizen zur Reaktion

Wird geladen…