N-bromobutanimide → 2-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide

HRID 1190135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190135
[CH3:1][N:2]([CH3:15])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:5])=[O:4].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[CH3:15][N:2]([CH3:1])[S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[C:12]([Br:23])[CH:13]=1)(=[O:4])=[O:5]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 589943702-(4-Amino-phenyl)-ethanesulfonic acid dimethylamide

Produkt 1

HCID 589943492-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamideAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 737 mg (3.23 mmol) of 2-(4-amino-phenyl)-ethanesulfonic acid dimethylamide (as prepared in the previous step) in CH2Cl2 (20 mL) was cooled to 0° C. and treated with 574 mg (3.23 mmol) of NBS. The ice bath was removed and the mixture stirred at RT for 25 min. The mixture was diluted with CH2Cl2 (40 mL) and washed with saturated aqueous NaHCO3 (2×30 mL). The aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers were dried (MgSO4) and concentrated in vacuo to afford 955 mg (96%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 7.35 (d, 1H, J=2.0 Hz), 7.04 (dd, 1H, J=8.0, 2.0 Hz), 4.44 (br s, 2H), 3.21-3.14 (m, 2H), 2.96-2.89 (m, 2H), 2.84 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C10H15N2OSBr, 307.0/309.0 (M+H). found 307.0/309.0.

Aufarbeitung

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with CH2Cl2 (40 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×30 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers
  5. dry with materialwere dried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-adb0f76cd7a14b9ea003fec346e365bf
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674100B2

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