Hydrochloric Acid → benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate

HRID 341797

Reaktionsgleichung

Reaktionsgleichung von HRID 341797
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl>C(Cl)Cl.O>[CH2:25]([O:24][C:22]([NH:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:12][CH:13]=1)=[NH:2])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformate2×HCID 222576054-Amidino benzyl azide

Produkt 1

HCID 140379073benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an additional 2 ml benzyl chloroformate was added and stirring was continued for another 30 minutes. Subsequently, water was added and the aqueous phase was adjusted to pH 7 with 2M HCl. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. 4-(benzyloxycarbonylamidino) benzyl azide was finally isolated as colorless crystals from ether/methylene chloride/hexane.

Aufarbeitung

  1. dry with materialthe resulting solution was dried (K2CO3)
  2. filtrationfiltered
  3. temperaturewas cooled in an ice bath
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6028a7b66c9e4b0a8bd9ebd60373e5f3
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856307

Verknüpfte Notizen

Wird geladen…