Sodium Iodide → HCID 178483981, Verbindung

HRID 25571

Reaktionsgleichung

Reaktionsgleichung von HRID 25571
[CH3:1][N:2]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9]OS(C2C=CC(C(F)(F)F)=CC=2)(=O)=O)[CH2:5][CH2:4]1.Cl.[CH3:38][N:39]([CH3:43])[CH2:40][CH2:41][SH:42].[H-].[Na+].[Na+].[I-].OS([O-])(=O)=O.[K+].C([O-])(O)=O.[Na+].CCOCC>CN(C=O)C>[CH3:38][N:39]([CH3:43])[CH2:40][CH2:41][S:42][CH2:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=2)(=[O:25])=[O:26])[CH2:4][CH2:5]1

Komponenten

8

Edukt 6

HCID 5238Sodium IodideHCID 24758Sodium hydride2×HCID 25798Captamine Hydrochloride2×HCID 516920Potassium bisulfateHCID 23682952Ether sodium bicarbonateHCID 178484820HCID 178484820, Verbindung

Produkt 1

HCID 178483981HCID 178483981, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 280 mg (0.5 mmol) of trans-4-Trifluoromethyl-benzenesulfonic acid 4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexylmethyl ester and 78 mg (0.55 mmol) of 2-dimethylaminoethanethiol hydrochloride in 4.5 ml DMF was treated at 0° C. with 48 mg (1.1 mmol) of 55% NaH, stirred for 20 h at RT. After cooling (0° C.) and treatment with a catalytic amount of NaI followed by 78 mg (0.55 mmol) of 2-dimethylaminoethanethiol hydrochloride and 48 mg (1.1 mmol) of 55% NaH the reaction mixture was stirred for 18 h at RT. The reaction was neutralized (aqueous 10% KHSO4, at 0° C.) and poured into aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution, dried over Na2SO4 and evaporated. Purification by flash column chromatography on silica gel with CH2Cl2/MeOH (95:5) yielded 138 mg (63%) of trans-N-[4-(2-Dimethylamino-ethylsulfanylmethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 439 (MH+).

Aufarbeitung

  1. stirringwas stirred for 18 h at RT
  2. washThe organic phases were washed with aqueous 10% NaCl solution
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customPurification by flash column chromatography on silica gel with CH2Cl2/MeOH (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-b359497fad8842908e41ec30d66d9a0f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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