Benzoic acid, 3-(chlorosulfonyl)- → 3-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acid

HRID 564567

Reaktionsgleichung

Reaktionsgleichung von HRID 564567
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl[S:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:14])=[O:13]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:10])[S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([OH:20])=[O:19])(=[O:14])=[O:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 457588Benzenemethanamine, 3-bromo-N-methyl-

Produkt 1

HCID 578132513-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acidAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(3-Bromophenyl)-N-methylmethanamine (0.100 g, 0.5 mmol) in DCM (5 mL) was added TEA (0.139 mL, 1.000 mmol) and 3-(chlorosulfonyl)benzoic acid (0.110 g, 0.500 mmol). The resulting mixture was stirred at room temperature for 0.5 h. The reaction was quenched with HCl (1 N), concentrated and redissolved in EtOAc (10 mL) which was washed with H2O (2×3 mL), brine (3 mL), then dried with Na2SO4. It was then filtered and concentrated to afford the title compound (0.1505 g, 78%). LC-MS m/z 384 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with HCl (1 N)
  2. concentrationconcentrated
  3. dissolutionredissolved in EtOAc (10 mL) which
  4. washwas washed with H2O (2×3 mL), brine (3 mL)
  5. dry with materialdried with Na2SO4
  6. filtrationIt was then filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-caa4573a80e24f40a34fe6341b29b0f6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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