Pyridine → Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate

HRID 1666341

Reaktionsgleichung

Reaktionsgleichung von HRID 1666341
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[N:2]1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C1COCC1.CC#N.C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:18](=[O:19])[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:9][C:4]=2[N:3]=[N:2]1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 178507366HCID 178507366, Verbindung

Produkt 1

HCID 178521835Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1H-benzo[d][1,2,3]triazol-5-amine (1.85 g, 13.8 mmol, Alfa Aesar) in THF (10 mL) and CH3CN (8 mL) was added pyridine (1.34 mL, 16.6 mmol) followed by phenyl chloroformate (2.27 mL, 14.5 mmol) slowly. The reaction was stirred overnight. The reaction was concentrated to give an oil, which was partitioned between CH2Cl2 and water. The organic layer was dried using a SPE phase separator and concentrated to give a solid. This was taken up in CH2Cl2 and the precipitate was filtered to give the desired product (2.0 g, 57%) which was used without purification. MS M+1: 256.06.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customto give an oil, which
  3. customwas partitioned between CH2Cl2 and water
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give a solid
  7. filtrationthe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-89dbd0b464a34d7d86d04e9bdc9844bb
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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