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Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1659746
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1659746
P(Cl)(Cl)([Cl:3])=O.[O:6]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][N:13]=[C:14]([C:18]2[N:19]=[C:20]([NH:23][CH:24]=[O:25])[S:21][CH:22]=2)[C:15]([OH:17])=O)=[N:7]1.[NH2:26][CH:27]1[C:47](=[O:48])[N:29]2[C:30]([C:44]([OH:46])=[O:45])=[C:31]([CH2:34][S:35][C:36]3[N:40]([CH2:41][CH:42]=[CH2:43])[N:39]=[N:38][N:37]=3)[CH2:32][S:33][C@H:28]12.[ClH:49]>O.CC(C)=O.C(OCC)(=O)C.C(N(CC)CC)C.O1CCCC1.CN(C)C=O>[CH3:28][N+:29]([CH3:47])=[CH:30][Cl:49].[Cl-:3].[O:6]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][N:13]=[C:14]([C:18]2[N:19]=[C:20]([NH:23][CH:24]=[O:25])[S:21][CH:22]=2)[C:15]([NH:26][CH:27]2[C:47](=[O:48])[N:29]3[C:30]([C:44]([OH:46])=[O:45])=[C:31]([CH2:34][S:35][C:36]4[N:40]([CH2:41][CH:42]=[CH2:43])[N:39]=[N:38][N:37]=4)[CH2:32][S:33][C@H:28]23)=[O:17])=[N:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

12

Edukt 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 537376352-(2-Formamidothiazol-4-yl)-2-[(3-isoxazolyl)methoxyimino]acetic acidHCID 704326537-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Produkt 2

HCID 77311Chloro-N,N-dimethylformiminium chloride
HCID 131712583
7-[2-(3-isoxazolyl)methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

The Vilsmeier reagent was prepared from dry dimethylformamide (0.74 g), phosphorus oxychloride (1.56 g) and dry ethyl acetate (2.0 ml) by the conventional method. Dry tetrahydrofuran (15 ml) was added thereto and then 2-(3-isoxazolyl)methoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.50 g) was added thereto at 0° C. The mixture was stirred for 30 minutes at the same temperature. The resulting mixture was added dropwise at -5° to 0° C. to a stirred solution of 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.34 g) in a mixture of water (11.5 ml) and acetone (11.5 ml) keeping the pH at 7.5 by triethylamine, and the mixture was stirred for 30 minutes at the same temperature at pH 7.5. To the reaction mixture was added ethyl acetate (60 ml) and the mixture was adjusted to pH 2.5 with 10% hydrochloric acid. Insoluble material was filtered off and the filtrate was extracted twice with ethyl acetate. The combined extracts were washed twice with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off and the residue was pulverized with diethyl ether to give yellowish powder of 7-[2-(3-isoxazolyl)methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.15 g).

Aufarbeitung

  1. customat 0° C
  2. stirringthe mixture was stirred for 30 minutes at the same temperature at pH 7.5
  3. filtrationInsoluble material was filtered off
  4. extractionthe filtrate was extracted twice with ethyl acetate
  5. washThe combined extracts were washed twice with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-631b09ac6142405fa0a72f9b5381ff56
Quelldatensatz
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04304770

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