Triethylamine → 3-Chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chloride

HRID 1808200

Reaktionsgleichung

Reaktionsgleichung von HRID 1808200
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([Cl:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25])[CH2:19][NH2:20].CCN(CC)CC>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([Cl:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:23]([C:24]([F:25])([F:26])[F:27])=[C:16]([Cl:15])[CH:17]=1)=[O:5]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 198147312-Chloro-4-(chlorosulfonyl)benzoyl chlorideHCID 235127443-Chloro-4-(trifluoromethyl)benzylamine

Produkt 1

HCID 577321163-Chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chlorideAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-(chlorosulfonyl)benzoyl chloride (J. Org. Chem, 56, 16, 1991, 4974) (300 mg, 0.877 mmol, 1 eq) in DCM (3 ml) was added 3-chloro-4-(trifluoromethyl)benzylamine (175 mg, 0.835 mmol, 0.95 eq) and Et3N (33 mg, 0.32 mmol, 0.37 eq) and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (10 ml), washed with water (10 ml), dried over sodium sulphate, filtered and evaporated. The crude material was purified by column chromatography eluting with ethyl acetate to yield the title compound (154 mg, 0.34 mmol, 39%).

Aufarbeitung

  1. washwashed with water (10 ml)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by column chromatography
  6. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-11d118631a774cb58f646d9633e23795
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357711B2

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