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Ethyl isocyanate → N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9103
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 9103
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].C(N(CC)CC)C>CN(C)C=O>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])[S:3][C:4]=2[CH:10]=1)#[N:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 43271392-Aminobenzothiazole-6-carbonitrile

Produkt 1

HCID 21985533N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Amino-1,3-benzothiazole-6-carbonitrile (0.2 g) was dissolved in about 5 mL dimethylformamide. About 0.2 mL of ethylisocyanate was added, followed by about 0.3 mL triethylamine and the solution was heated to about 80° C. under good agitation. The solution was allowed to stir for about 4 hours then cooled to room temperature. The solvent was removed in vacuo and the solids were washed well with ether. The product was further purified by column chromatography and after drying in vacuo, about 0.14 grams was isolated. 1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. washthe solids were washed well with ether
  4. customThe product was further purified by column chromatography
  5. customafter drying in vacuo
  6. customabout 0.14 grams was isolated
  7. custom1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes

Quellen und Nachweise

ORD-Eintrag
ord-4bb201544c5043cd978fe2b16f5062ab
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091227B2

Notizen zur Reaktion

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