Diisopropylethylamine → N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

HRID 1665002

Reaktionsgleichung

Reaktionsgleichung von HRID 1665002
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:22])([F:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18].C(N(C(C)C)C(C)C)C>ClCCl>[Br:1][C:2]1[S:6][C:5]([CH2:7][NH:8][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([F:9])([F:21])[F:22])(=[O:19])=[O:18])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 23130577(5-Bromothiophen-2-yl)methanamine

Produkt 1

HCID 35408897N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamideAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 1-(5-bromo-2-thienyl)-methanamine (0.5 g) in dichloromethane (8 mL) were added 2-(trifluoromethyl)-benzenesulfonyl chloride (0.67 g) and N-ethyl-diisopropylamine (0.37 g) at 0° C. After stirring for 10 min, the ice bath was removed and the mixture was stirred for 40 min. The reaction mixture was diluted with dichloromethane and washed with 0.5 M HCl and with water. The organic phase was dried (MgSO4), filtered and concentrated. The residue was suspended in cyclohexane. The solid was collected by filtration and dried to give N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (0.596 g) as a colorless solid. MS: 417.1 ([M+NH4]+)

Aufarbeitung

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred for 40 min
  3. additionThe reaction mixture was diluted with dichloromethane
  4. washwashed with 0.5 M HCl and with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe solid was collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dc894f865cda4f85bea1c75c570400e6
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039493B2

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