Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1074941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074941
P(Cl)(Cl)([Cl:3])=O.[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([OH:16])=O)[CH2:10][CH2:9][CH:8]=[CH:7]1.[ClH:25].C1(ON)CCCC=C1.[NH2:34][CH:35]1[C:56](=[O:57])[N:37]2[C:38]([C:53]([OH:55])=[O:54])=[C:39]([CH2:42][S:43][C:44]3[CH:45]=[CH:46][C:47]4[N:48]([N:50]=[N:51][N:52]=4)[N:49]=3)[CH2:40][S:41][C@H:36]12.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C.CC(C)=O.CN(C)C=O>[CH3:36][N+:37]([CH3:56])=[CH:38][Cl:25].[Cl-:3].[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([NH:34][CH:35]2[C:56](=[O:57])[N:37]3[C:38]([C:53]([OH:55])=[O:54])=[C:39]([CH2:42][S:43][C:44]4[CH:45]=[CH:46][C:47]5[N:48]([N:50]=[N:51][N:52]=5)[N:49]=4)[CH2:40][S:41][C@H:36]23)=[O:16])[CH2:10][CH2:9][CH:8]=[CH:7]1

Komponenten

14

Edukt 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 13345661HCID 13345661, VerbindungHCID 20274566(2-Cyclohexen-1-yl)oxyamine hydrochloride2×HCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid

Produkt 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317130267-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
-3 °C

Versuchsvorschrift

The solution of Vilsmeier reagent was prepared from dry N,N-dimethylformamide (0.4 g), phosphoryl chloride (0.8 ) and dry ethyl acetate (1.6 ml) in a usual manner. To the solution were added dry tetrahydrofuran (18 ml) and 2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.2 g) and then stirred at -3° to 3° C. (Solution A). A mixture of 7-amino-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (1.5 g), sodium carbonate (0.9 g) and water (9.0 ml) was stirred to give a homogeneous solution. After the addition of acetone (9.0 ml), the solution was cooled to -3° C. and then thereto was added Solution A over a period of 5 minutes, keeping the temperature at -3° to 3° C. and the pH at 7.5 to 8.5 with triethyl amine. The resulting mixture was stirred for 30 minutes at the same temperature and pH. To the reaction mixture were added water, ethyl acetate and tetrahydrofuran. The resulting mixture was adjusted to pH 2.0 with 10% hydrochloric acid and filtered. The organic layer was separated from the filtrate, washed with water (×3), dried over magnesium sulfate, treated with activated charcoal and then evaporated. The residue was pulverized in isopropyl ether. The powder was collected by filtration, washed with isopropyl ether and then dried to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.83 g).

Aufarbeitung

  1. customto give a homogeneous solution
  2. customat -3° to 3° C.
  3. stirringThe resulting mixture was stirred for 30 minutes at the same temperature and pH
  4. filtrationfiltered
  5. customThe organic layer was separated from the filtrate
  6. washwashed with water (×3)
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated
  10. filtrationThe powder was collected by filtration
  11. washwashed with isopropyl ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0275ec594ee9443a818b08993d6467c5
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04394384

Notizen zur Reaktion

Wird geladen…