Dichloromethane → 2-bromo-N-tert-butylbenzenesulfonamide

HRID 447225

Reaktionsgleichung

Reaktionsgleichung von HRID 447225
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].C(Cl)Cl.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:10])=[O:9]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chloride

Produkt 1

HCID 48250142-bromo-N-tert-butylbenzenesulfonamideAusbeute 97,1 %

Versuchsvorschrift

2-Bromobenzenesulfonyl chloride (100.9 g, 394.9 mmol) was dissolved in DCM (500 mL, 8.0 mol) and cooled at 0° C. t-Butylamine (41.3 mL, 395 mmol) was added in 3 portions over approximately 1 minute. DIPEA (75.7 mL, 434 mmol) was immediately added in 3 portions over approximately 1 minute. The mixture was warmed to room temperature and stirred overnight. The product was washed with 1M H3PO4 (2×), with saturated. NaHCO3, and with saturated aqueous NaCl, then dried over MgSO4, filtered, and concentrated to yield 2-bromo-N-t-butyl-benzenesulfonamide (112 g) as a light brown solid.

Aufarbeitung

  1. additionwas added in 3 portions over approximately 1 minute
  2. washThe product was washed with 1M H3PO4 (2×)
  3. dry with materialNaHCO3, and with saturated aqueous NaCl, then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d770688ee8214b06a1d4517698898d3f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481549B2

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