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

HRID 22476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 22476
[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.[Cl:14]C(OC(Cl)(Cl)Cl)=O.CN(C)C=O>O1CCCC1>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([Cl:14])=[O:9])[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 10426DiphosgeneHCID 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 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 30.0 ml of tetrahydrofuran (THF), 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 5.43 g of trichloromethyl chloroformate at 5° C. to a mixture of 80 ml of THF and 4.0 g of N,N-dimethylformamide (DMF) and then reacting them for 30 minutes. After they were reacted for 5 minutes, the reaction mixture was poured into 200 ml of ice water to precipitate crystals. The crystals were collected by filtration, washed with 100 ml of ice water, collected by filtration, 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: 9.2 g (84.3%). Purity: 96.5%.

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. filtrationcollected by filtration
  9. filtrationAfter filtration
  10. dry with materialthe resulting crystals were dried under reduced pressure, whereby the title compound
  11. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-acac927768954aa6bcf8906d5dea0427
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05428173

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