Triethylamine → 1-(6-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

HRID 9129

Reaktionsgleichung

Reaktionsgleichung von HRID 9129
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>CN(C=O)C.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][Si:25]([C:28]#[C:29][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1)([CH3:27])[CH3:26]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylurea

Produkt 1

HCID 219855421-(6-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylureaAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.33 mmol), Pd(PPh3)2Cl2 (0.012 g, 0.017 mmol, 0.05 eq), and triethylamine (0.20 mL, 1.42 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for about 5 minutes, followed by the addition of trimethylsilyl acetylene (0.23 mL, 1.65 mmol, 5.0 eq). The mixture was heated at about 80° C. with stirring in a sealed tube for about 15 hours. The mixture was cooled down, taken up in 10 mL MeOH, and evaporated to dryness. Purification by HPLC gave pure desired compound 0.093 g (89%). LC/MS 318 (M+1); LC retention time 3.77 min.

Aufarbeitung

  1. customwas bubbled with nitrogen gas for about 5 minutes
  2. temperatureThe mixture was cooled down
  3. customevaporated to dryness
  4. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-257621e7b77e496c8a6049834742adcb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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