Triethylamine → (NE)-N-[(2-iodophenyl)methylidene]-4-(trifluoromethyl)benzenesulfonamide

HRID 2061589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061589
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C1COCC1.[Ti](Cl)(Cl)(Cl)Cl>[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[N:21]/[S:18]([C:15]1[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:23])[F:22])=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 700184-(Trifluoromethyl)benzenesulfonamideHCID 6434392-Iodobenzaldehyde

Produkt 1

HCID 59268908(NE)-N-[(2-iodophenyl)methylidene]-4-(trifluoromethyl)benzenesulfonamideAusbeute 116 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the mixture of 2-iodobenzaldehyde (11) (12.3 g, 53 mmol) and 4-trifluoromethylbenzenesulfonamide (12) (12.15 g, 54 mmol) in CH2Cl2 (110 mL) and THF (27 mL) was added triethylamine (22.5 mL) and titanium(IV) chloride (3 mL) at 0° C. After stirring at 0° C. for 2 h, the solid was separated via Celite filtration. The filtrate was concentrated under reduced pressure to dryness, triturated with toluene to give 27 g of a yellow solid as the crude product (3) which was used without further purification.

Aufarbeitung

  1. customthe solid was separated via Celite filtration
  2. concentrationThe filtrate was concentrated under reduced pressure to dryness
  3. customtriturated with toluene

Quellen und Nachweise

ORD-Eintrag
ord-3208e37bc4e443c8844a8322d7ba3ca7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283358B2

Notizen zur Reaktion

Wird geladen…