Triethylamine → 1-ethoxycarbonyloxy-6-chloro1H-benzotriazole

HRID 597692

Reaktionsgleichung

Reaktionsgleichung von HRID 597692
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([O:4][C:2]([O:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1)=[O:3])[CH3:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Produkt 1

HCID 132928531-ethoxycarbonyloxy-6-chloro1H-benzotriazoleAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel3×

Versuchsvorschrift

A solution of ethyl chloroformate (2.17 g.) in benzene (10 ml.) was added dropwise to a solution of 1-hydroxy-6-chloro-1H-benzotriazole (3.38 g.) and triethylamine (2.80 ml.) in benzene (30 ml.) under ice-cooling and stirring. Benzene (30 ml.) was further added to the mixture and the reaction temperature was slowly elevated to room temperature the mixture was allowed to stand overnight. Precipitated crystals were filtered off and the filtrate was concentrated. Benzene was added to the residue and an insoluble material was filtered off. The filtrate was concentrated to give 1-ethoxycarbonyloxy-6-chloro1H-benzotriazole (2.2 g.), crystals. The precipitated crystals filtered off and the insoluble material in benzene were mixed and then washed with water, a sodium bicarbonate aqueous solution, 1N hydrochloric acid and water, and recrystallized from methanol (75 ml.) to give the desired compound (3.5 g.), white needles, mp 160° to 162° C.

Aufarbeitung

  1. temperaturecooling
  2. customwas slowly elevated to room temperature
  3. customPrecipitated crystals
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated
  6. additionBenzene was added to the residue
  7. filtrationan insoluble material was filtered off
  8. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9d4deea5a1ce4862b6a56f488fac89a3
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014915

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