Thionyl Chloride → 2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride

HRID 2295633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295633
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10](O)=[O:11])[N:8]=1)=[O:2].S(Cl)([Cl:18])=O>CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([Cl:18])=[O:11])[N:8]=1)=[O:2]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 27245112-(2-Formylamino-1,3-Thiazol-4-Yl)-2-(Methoxyimino)Acetic Acid

Produkt 1

HCID 537143512-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N,N-Dimethylformamide (3 drops) was added to a suspension of 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 23 g.) in thionyl chloride (230 ml.), and stirred at 60° C. for 5 minutes. After concentrating the solution in vacuo, benzene was added to the residue. The presipitates were collected by filtration, washed with benzene (30 ml.) three times and diethyl ether in turn to give 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 18 g.). On the other hand, trimethylsilylacetamide (46 g.) was added to a suspension of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (16.8 g.) in methylene chloride (168 ml.), and stirred at 40° C. for an hour. To the suspension was gradually added 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 13.6 g.) at -5° to 0° C., and stirred at the same temperature for an hour. Water (150 ml.) was added to the resultant solution and stirred for 15 minutes. The recipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (anti isomer, 25.7 g.).

Aufarbeitung

  1. concentrationAfter concentrating the solution in vacuo, benzene
  2. additionwas added to the residue
  3. filtrationThe presipitates were collected by filtration
  4. washwashed with benzene (30 ml.) three times and diethyl ether in turn

Quellen und Nachweise

ORD-Eintrag
ord-115bbbfcba614e4e9f3573c582350ab2
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04425341

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