Oxalyl chloride → Ethyl 6,8-dichloro-7-(4-(4-chlorophenethylcarbamoyl)phenoxy)chroman-4-carboxylate

HRID 510659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510659
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(Cl)(=O)C(Cl)=O.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][NH2:43])=[CH:37][CH:36]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17](=[O:19])[NH:43][CH2:42][CH2:41][C:38]3[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=3)=[CH:20][CH:21]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 670803034-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Produkt 1

HCID 67080461Ethyl 6,8-dichloro-7-(4-(4-chlorophenethylcarbamoyl)phenoxy)chroman-4-carboxylateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (22.96 g, 55.832 mmol) was dissolved in dichloromethane (200 ml) and DMF (0.2 ml). Oxalyl chloride (8.6 ml, 98.585 mmol) was added slowly over a period of 30 minutes at ambient temperature. The crude mixture was concentrated under reduced pressure. Dry dichloromethane (200 ml) was added and the mixture was cooled in an ice bath. 2-(4-Chlorophenyl)ethylamine (8.5413 ml, 61.415 mmol) and diisopropylethylamine (11.701 ml, 66.999 mmol) were added sequentially to the mixture. The mixture was stirred in an ice bath for 10 minutes and warmed to ambient temperature. The crude mixture was washed with 1N HCl (100 ml), water (2×50 ml), and brine (50 ml), dried over MgSO4, filtered through GF paper, and concentrated to provide 30.1 g of a light brown solid after drying under high vacuum for 2 hours. The crude solid was recrystallized from hot EtOAc-hexanes to provide 26.8 g of the title compound as a light brown solid (87%).

Aufarbeitung

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. additionDry dichloromethane (200 ml) was added
  3. temperaturethe mixture was cooled in an ice bath
  4. washThe crude mixture was washed with 1N HCl (100 ml), water (2×50 ml), and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through GF paper
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-28056163474f459e867eed1f0a4f6068
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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