Toluene → 4-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 501512

Reaktionsgleichung

Reaktionsgleichung von HRID 501512
Cl.[NH2:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1.[C:15]([O-])(O)=[O:16].[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[N:2]([C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)=[C:15]=[O:16]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 1317269774-Amino-5,6,7,8-tetrahydronaphthalene-1-carbonitrile, hydrochloride salt

Produkt 1

HCID 597543044-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrileAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirring suspension of compound 2D (0.10 g, 0.48 mmol) and NaHCO3 (0.404 g, 4.80 mmol) in CH2Cl2 (4 mL) cooled to 0° C. was rapidly added a solution of phosgene (20%) in toluene (0.95 mL, 4.32 mmol). After addition, the mixture was stirred at rt for 2 h, then filtered to remove the solid. The filtrate was concentrated under reduced pressure, the resulting solid residue dried under vacuum for 1 h to afford compound 2E (95 mg) as a light yellow solid.

Aufarbeitung

  1. additionAfter addition
  2. filtrationfiltered
  3. customto remove the solid
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting solid residue dried under vacuum for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-d93fd10229394289bffabb38e613fd6d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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