Oxalyl chloride → (R)-N-(2-chloro4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 841196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841196
C(Cl)(=O)C(Cl)=O.[OH:7][C@@:8]([CH3:16])([C:12]([F:15])([F:14])[F:13])[C:9](O)=[O:10].[Cl:17][C:18]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:19]=1[NH2:20].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>ClCCl.CN(C=O)C>[Cl:17][C:18]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:19]=1[NH:20][C:9](=[O:10])[C@:8]([OH:7])([CH3:16])[C:12]([F:15])([F:14])[F:13]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 685102,6-Di-tert-butylpyridineHCID 2829302-Chloro-4-iodoanilineHCID 2760712(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

Produkt 1

HCID 54268602(R)-N-(2-chloro4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (1.07 ml) was added dropwise to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 9) (1.95 g) in dichloromethane (42 ml) and DMF (0.8 ml). The mixture was stirred at ambient temperature for 2 hours and was then added over 35 minutes to a solution of 2-chloro-4-iodoaniline (2.5 g) and 2,6-di-tert-butylpyridine (2.94 ml) in dichloromethane (40 ml) and stirred a further 18 hours. Volatile material was removed by evaporation and the residue was purified by flash chromatography on silica gel eluting with dichloromethane to give the title compound (2.85 g) as a solid. NMR: 1.6 (s, 3H), 7.7 (m, 2H), 7.8 (d, 1H), 7.9 (br s, 1H); MS: 392 (M−H)−.

Aufarbeitung

  1. stirringstirred a further 18 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was purified by flash chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ebc9cd2444294208bcfa93fe8de8337a
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369273B1

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