Dimethylamine → N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamide

HRID 1284822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1284822
[CH3:1][C:2]1[C:7]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:6]([CH3:16])[CH:5]=[CH:4][C:3]=1[S:17](Cl)(=[O:19])=[O:18].[CH3:21][NH:22][CH3:23]>O1CCCC1>[CH3:21][N:22]([CH3:23])[S:17]([C:3]1[CH:4]=[CH:5][C:6]([CH3:16])=[C:7]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[C:2]=1[CH3:1])(=[O:19])=[O:18]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 135378902,4-Dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonyl chloride

Produkt 1

HCID 13300593N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamideAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,4-Dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.4 g) was added to tetrahydrofuran (20 ml) containing dimethylamine (0.6 g), and the resultant mixture was allowed to stand overnight at room temperature. The reaction mixture was concentrated, admixed with 5% hydrochloric acid and extracted with chloroform. The extract was washed with 5% hydrochloric acid and water in order, dried over anhydrous magnesium sulfate and concentrated to give an oily substance, which was purified by column chromatography with silica gel (150 ml) to give 1.0 g of N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamide. M.P., 70.5°-72° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washThe extract was washed with 5% hydrochloric acid and water in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oily substance, which
  7. customwas purified by column chromatography with silica gel (150 ml)

Quellen und Nachweise

ORD-Eintrag
ord-52d8f37eff5a4fc0b547c090268cedcd
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04564386

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