Triethylamine → (3-Chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester

HRID 1019207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019207
[CH3:1][O:2][C:3](=[O:28])[C:4]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([Cl:27])[CH:18]=1)=[N:5][NH:6]S(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:28])[C:4]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([Cl:27])[CH:18]=1)=[N+:5]=[N-:6]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 86584878(3-Chloro-4-methanesulfonyl-phenyl)-(4-toluenesulfonyl-hydrazono)-acetic acid methyl ester

Produkt 1

HCID 86584876(3-Chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl esterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3-chloro-4-methanesulfonyl-phenyl)-(4-toluenesulfonyl-hydrazono)-acetic acid methyl ester (3.82 g, 8.5 mmol) and triethylamine (1.3 mL, 9.35 mmol) in dichloromethane (40 mL) was stirred at 25° C. After 1 h, the reaction was evaporated under reduced pressure and the resulting residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ ethyl acetate) to give (3-chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester (978 mg, 40% yield) as a bright yellowish orange solid, mp 102.7-106.5° C.; EI-HRMS m/e calcd for C10H9N2ClSO4 (M+) 287.9972, found 287.9979.

Aufarbeitung

  1. customthe reaction was evaporated under reduced pressure
  2. customthe resulting residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-62edb96fb8d346e99b3b18a0f6674a63
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486184B2

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