Phenyl isocyanate → (S)-(6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-3-phenylurea

HRID 2234254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234254
[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[NH:4][CH2:3]1.[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH2:3][C@@H:2]([NH:1][C:21]([NH:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22])[CH2:11]2)#[N:13]

Komponenten

4

Edukt 2

HCID 7672Phenyl isocyanateHCID 66757521(S)-3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Produkt 1

HCID 68581279(S)-(6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-3-phenylureaAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile (52 mg, 0.3 mmol), prepared as described in Example 1F, in CH2Cl2 (2 mL) at RT was added phenyl isocyanate (33 μl, 0.3 mmol) dropwise. After addition, the reaction was stirred at RT for 1 h. The product was collected by filtration and washed with CH2Cl2-hexanes (1:1) to give the title compound (85 mg, 97%) as a white solid.

Aufarbeitung

  1. additionAfter addition
  2. filtrationThe product was collected by filtration
  3. washwashed with CH2Cl2-hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-04b3c0ce16c34ef4b9184006199c6459
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709647B2

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