Diisopropylethylamine → HCID 178464644, Verbindung

HRID 12513

Reaktionsgleichung

Reaktionsgleichung von HRID 12513
Cl.[CH2:2]([CH:4]1[CH2:8][N:7]([C:9]([NH:11][CH2:12][CH3:13])=[NH:10])[N:6]=[CH:5]1)[CH3:3].CCN(C(C)C)C(C)C.[N:23]1[S:27][N:26]=[C:25]2[C:28]([S:32](Cl)(=[O:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:24]=12>C(Cl)Cl>[CH2:12]([NH:11][C:9]([N:7]1[CH2:8][CH:4]([CH2:2][CH3:3])[CH:5]=[N:6]1)=[N:10][S:32]([C:28]1[C:25]2=[N:26][S:27][N:23]=[C:24]2[CH:31]=[CH:30][CH:29]=1)(=[O:34])=[O:33])[CH3:13]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-HCID 178464604HCID 178464604, Verbindung

Produkt 1

HCID 178464644HCID 178464644, VerbindungAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

300 mg 4,N-Diethyl-4,5-dihydro-pyrazole-1-carboxamidine hydrochloride was suspended in 10 mL DCM. 0.53 mL DiPEA and 310 mg benzo[1,2,5]thiadiazole-4-sulfonylchloride were added and the mixture was stirred overnight at room temperature. The mixture was washed with 5% NaHCO3 and 2 M NaOH, the organic layer dried over Na2SO4 and the solvent evaporated in vacuo to yield 410 mg of a red/brown oil. The crude product was purified by flash chromatography (DCM:aceton=98:2, Rf=0.18) to yield 350 mg (65%) of an orange oil. 1H NMR (400 MHz, CDCl3) δ 0.93 (t, J=7.5 Hz, 3H), 1.16 (br t, J=7 Hz, 3H), 1.41-1.66 (m, 2H), 3.01-3.16 (m, 1H), 3.39-3.55 (m, 2H), 3.59-3.74 (m, 1H), 3.95-4.15 (m, 1H), 6.94 (br s, 1H), 6.95 (br s, 1H), 7.68 (dd, J=9 and 7 Hz, 1H), 8.15 (br d, J=9 Hz, 1H), 8.31 (br d, J=7 Hz, 1H).

Aufarbeitung

  1. washThe mixture was washed with 5% NaHCO3 and 2 M NaOH
  2. dry with materialthe organic layer dried over Na2SO4
  3. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee39ee2d9b114f3a936d102e63da2c71
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

Verknüpfte Notizen

Wird geladen…