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Oxalyl chloride → HCID 58488524, Verbindung

HRID 451368
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 451368
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([OH:16])=O)[C:10]=1[CH3:17].C(Cl)(=O)C(Cl)=O.Cl.[CH3:25][S:26]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].CCN(C(C)C)C(C)C>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([NH:33][C:32]2[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:35][CH:34]=2)=[O:16])[C:10]=1[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 58488523HCID 58488523, Verbindung

Produkt 1

HCID 58488524HCID 58488524, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylic acid (0.61 g, 2.4 mmol) in dichloromethane (30 ml) was added oxalyl chloride (0.41 ml, 4.8 mmol). The mixture was stirred at room temperature for 2.0 h, after which time the solvent was removed on a rotary evaporator. To this brown residue was added THF (40 ml), 4-(methanesulfonyl)aniline hydrochloride (495 mg, 2.38 mmol), and DIEA (1.6 ml, 9.5 mmol). The solution was stirred at room temperature for 20 h. The reaction mixture was concentrated on a rotary evaporator and 2N HCl (30 ml) was added to the residue. The solid was filtered and washed with 2N HCl, water and IPE to give the title compound (812 mg, 84%) as a brown solid.

Aufarbeitung

  1. customafter which time the solvent was removed on a rotary evaporator
  2. stirringThe solution was stirred at room temperature for 20 h
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator and 2N HCl (30 ml)
  4. additionwas added to the residue
  5. filtrationThe solid was filtered
  6. washwashed with 2N HCl, water and IPE

Quellen und Nachweise

ORD-Eintrag
ord-d75ee2fec5bc4710bc546c922848871f
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08487117B2

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