Aluminium lithium hydride → N-[6-(Aminomethyl)-1,3-benzothiazol-2-yl]-N'-ethylurea

HRID 9174

Reaktionsgleichung

Reaktionsgleichung von HRID 9174
[C:1]([C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[S:9][C:5]=2[CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>COCCOC>[NH2:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[S:9][C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 21985533N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

Produkt 1

HCID 21985534N-[6-(Aminomethyl)-1,3-benzothiazol-2-yl]-N'-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

About 0.05 g of N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 10 mL of ethyleneglycol dimethylether. Introduced about 50 mg lithium aluminum hydride in several portions over about 12–24 hours. The slurry was quenched with about 5–10 mL ethyl acetate then about 1–2 mL of saturated aqueous sodium sulfate. The slurry was then diluted with water and extracted with ethyl acetate. Following drying and removal of solvents under reduced pressure, the product was isolated by preparative HPLC. 1H NMR 1.08 (t, 3H), 1.88 (s, 3H), 3.17 (m, 2H), 3.83 (s, 2H), 7.07 (m, 1H), 7.32 (m, 1H), 7.54 (d, 1H), 7.8 (s, 1H); LC/MS 1.86 min, 251 (M+1), 249 (M−1).

Aufarbeitung

  1. customThe slurry was quenched with about 5–10 mL ethyl acetate
  2. additionThe slurry was then diluted with water
  3. extractionextracted with ethyl acetate
  4. customFollowing drying
  5. customremoval of solvents under reduced pressure
  6. customthe product was isolated by preparative HPLC
  7. customLC/MS 1.86 min, 251 (M+1), 249 (M−1)

Quellen und Nachweise

ORD-Eintrag
ord-032960dec0b94b21ba18a8f769a61520
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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