Phenyl isocyanate → 1-(6-(3-Phenylaminocarbonylamino-propanoyl)-2-benzothiazolyl)-3-ethylurea

HRID 9140

Reaktionsgleichung

Reaktionsgleichung von HRID 9140
[NH2:1][CH2:2][CH2:3][C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5].C(N(CC)CC)C.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[C:28]1([NH:34][C:35]([NH:1][CH2:2][CH2:3][C:4]([C:6]2[CH:20]=[CH:19][C:9]3[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=3[CH:7]=2)=[O:5])=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 219855561-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylurea

Produkt 1

HCID 219855861-(6-(3-Phenylaminocarbonylamino-propanoyl)-2-benzothiazolyl)-3-ethylureaAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea (0.033 g, 0.10 mmol) in 1 mL anhydrous DMF was treated with triethylamine (0.028 mL, 0.20 mmol, 2.0 eq) at room temperature. It was stirred for about 5 min, followed by the addition of phenyl isocyanate (0.013 mL, 0.12 mmol, 1.2 eq). It was stirred for about 2.5 hours, quenched with MeOH, filtered, concentrated, and purified by HPLC to give the desired compound 0.009 g (22%). LC/MS 412.2 (M+1); LC retention time 2.80 min.

Aufarbeitung

  1. stirringIt was stirred for about 2.5 hours
  2. customquenched with MeOH
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7c11d59354d54b46b7c009458d9fc655
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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