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Dimethylformamide → (2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl chloride

HRID 22473
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 22473
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8](O)=[O:9])[N:3]=1.P(Cl)(Cl)([Cl:16])=O.CN(C)C=O>C(#N)C>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([Cl:16])=[O:9])[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 101304122-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid

Produkt 1

HCID 10198354(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

In 80.0 ml of acetonitrile, 10.0 g of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetic acid were stirred at -20° C., followed by the dropwise addition of a chlorinating reagent, which had been prepared beforehand by gradually adding 8.4 g of phosphorus oxychloride at 5° C. to a mixture of 25 ml of acetonitrile and 4.0 g of N,N-dimethylformamide (DMF) and then reacting them for 30 minutes. After they were reacted for 5 minutes, 200 ml of ice water were poured into the reaction mixture to precipitate crystals. The crystals were collected by filtration, washed with 100 ml of ice water and then stirred for 30 minutes in 100 ml of n-hexane. After filtration, the resulting crystals were dried under reduced pressure, whereby the title compound was obtained. Yield: 8.90 g (81.6%). Purity: 97.9%.

Aufarbeitung

  1. additionfollowed by the dropwise addition of a chlorinating reagent, which
  2. customhad been prepared beforehand
  3. customfor 30 minutes
  4. customAfter they were reacted for 5 minutes
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with 100 ml of ice water
  8. filtrationAfter filtration
  9. dry with materialthe resulting crystals were dried under reduced pressure, whereby the title compound
  10. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-6be2842cade74a07965584b849ce990d
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05428173

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