Benzene → 1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

HRID 596216

Reaktionsgleichung

Reaktionsgleichung von HRID 596216
[C:1](Cl)(Cl)=O.[OH:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.Cl[C:17]([O:19]N1C2C=C(Cl)C=CC=2N=N1)=[O:18].[CH:30]1[CH:35]=[CH:34]C=CC=1>N1C=CC=CC=1.C(O)(C)(C)C>[C:35]([O:19][C:17]([O:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1)=[O:18])([CH3:34])([CH3:30])[CH3:1]

Komponenten

7

Edukt 4

HCID 241Benzene3×HCID 6371PhosgeneHCID 2327116-Chloro-1-hydroxy-1H-benzotriazoleHCID 205679821-chlorocarbonyloxy-6-chloro-1H-benzotriazole

Produkt 1

HCID 132928521-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A solution of phosgene (5 g.) in benzene (23.5 ml.) was dropwise added under ice-cooling to a suspension of 1-hydroxy-6-chloro-1H-benzotriazole (8.5 g.) and pyridine (3.9 g.) in benzene (50 ml.), and the mixture was stirred for 30 minutes at the same temperature and allowed to stand overnight. To the resultant solution containing 1-chlorocarbonyloxy-6-chloro-1H-benzotriazole was dropwise added, over 20 minutes under ice-cooling, a solution of tert-butyl alcohol (3.7 g.) and pyridine (4.0 g.) in benzene (50 ml.). The resultant mixture was stirred for 2 hours at the same temperature and allowed to stand overnight. The reaction mixture was filtered, and the filtrate was concentrated. Ether and petroleum ether were added to the residue to pulverize the residue and obtained crystals were collected by filtration to give 1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole (5.3 g.). The mother liquor was concentrated to give the same object compound (0.6 g.). Both crystals were put together and dissolved in benzene, after which the solution was washed with a sodium bicarbonate aqueous solution and water and then dried. The solvent was removed by distillation to give the object compound (3.2 g.), powder, mp 98° to 100° C (dec.).

Aufarbeitung

  1. waitto stand overnight
  2. additionwas dropwise added, over 20 minutes under ice-
  3. temperaturecooling
  4. waitto stand overnight
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. additionEther and petroleum ether were added to the residue
  8. customobtained crystals
  9. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1869df57661f4238a3d6a58ae4e3e5fe
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010178

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