Dimethyl Sulfoxide → HCID 19966225, Verbindung

HRID 1734899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734899
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:17][C:16]=1[NH:25][C:26](=[O:42])[CH2:27][CH:28]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:35][C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(OCC)C.C(Cl)Cl>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][C:16]=1[NH:25][C:26](=[O:42])[CH2:27][CH:28]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:35][C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)([CH3:14])([CH3:12])[CH3:13]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19966239N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

Produkt 1

HCID 19966225HCID 19966225, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2 ml of a methylene chloride solution containing 155 mg (1.98 mmol) of dimethyl sulfoxide were added dropwise over a period of 5 minutes to 2 ml of a methylene chloride solution containing 126 mg (0.99 mmol) of oxalyl chloride which had previously been cooled at -78° C. The mixture was then stirred for 5 minutes at this temperature, after which 15 ml of a methylene chloride solution containing 354 mg (0.825 mmol) of N-[2-t-butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 18) were added, and the mixture was stirred for a further 15 minutes at this temperature. 501 mg (4.95 mmol) of triethylamine were then added to the reaction mixture, which was then stirred for 5 minutes at the same temperature. The reaction mixture was then allowed to return to room temperature, after which it was diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution with a 100:5 by volume mixture of methylene chloride and ethyl acetate afforded 310 mg (yield 88%) of the title compound as crystals, melting at 176°-177° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred for a further 15 minutes at this temperature
  3. stirringwas then stirred for 5 minutes at the same temperature
  4. customto return to room temperature
  5. washwashed with dilute aqueous hydrochloric acid
  6. customThe solvent was then removed by distillation under reduced pressure
  7. washElution with a 100:5
  8. additionby volume mixture of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-95097c0e3e49464fb770eda4bca47def
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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