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Pyridine → Ethyl 2-methanesulfonamidothiazol-5-ylacetate

HRID 127104
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 127104
[NH2:1][C:2]1[S:3][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][N:6]=1.N1C=CC=CC=1.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>C(Cl)Cl>[CH3:22][S:19]([NH:1][C:2]1[S:3][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][N:6]=1)(=[O:21])=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 717815Ethyl 2-(2-amino-1,3-thiazol-5-yl)acetate

Produkt 1

HCID 20288652Ethyl 2-methanesulfonamidothiazol-5-ylacetateAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of ethyl 2-aminothiazol-5-ylacetate (32 g.) in methylene chloride (160 ml.) was added pyridine (27.2 g.) under ice-cooling, and to the mixture was dropwise added mesyl chloride (29.6 g.) in methylene chloride (29.6 ml.) over 30 minutes at 8° to 10° C. The mixture was further stirred for 8 hours at room temperature. After the reaction, methylene chloride was distilled off from the reaction mixture, and to the residue were added water (300 ml.) and ethyl acetate (300 ml.). The resulting mixture was adjusted to pH 2 with 10% hydrochloric acid under ice-cooling, and the precipitates were collected by filtration and washed with ethyl acetate. The precipitates were recrystallized from ethanol (600 ml.) to give ethyl 2-methanesulfonamidothiazol-5-ylacetate (27.3 g.), mp 153° to 155° C.

Aufarbeitung

  1. temperaturecooling
  2. customover 30 minutes
  3. customat 8° to 10° C
  4. distillationwas distilled off from the reaction mixture
  5. additionto the residue were added water (300 ml.) and ethyl acetate (300 ml.)
  6. temperaturecooling
  7. filtrationthe precipitates were collected by filtration
  8. washwashed with ethyl acetate
  9. customThe precipitates were recrystallized from ethanol (600 ml.)

Quellen und Nachweise

ORD-Eintrag
ord-3dad1036b9dd452d961c4d42bc138ca6
Quelldatensatz
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04254260

Notizen zur Reaktion

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