Water → HCID 21997544, Verbindung

HRID 1977262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977262
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:13]([C:14]([NH:16][NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)=O)=[CH:12][CH:11]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:33].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:13]([C:14]2[S:33][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)=[N:17][N:16]=2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 21997580HCID 21997580, Verbindung

Produkt 1

HCID 21997544HCID 21997544, VerbindungAusbeute 165,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of N-[4-(6-methoxy-n-hexyloxy)benzoyl]-N′-(4-methoxycarbonylbenzoyl)hydrazine (193.4 g) and phosphorus pentasulfide (113.34 g) in tetrahydrofuran (2.5 L) was heated to reflux for 1 hour then cooled to room temperature and poured into water (7 L). The resulting precipitate was collected by filtration, washed thoroughly with water then partially dried. The solid was added to 1:1 CH3CN—H2O (200 ml), sitrred then filtered. This procedure was repeated a further 2 times, and the resulting yellow powder washed thoroughly with acetonitrile (500 ml×5) then dried under hi-vacuum at 50° C. to give methyl 4-[5-[4-(6-methoxy-n-hexyloxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoate (179.6 g) as a yellow powder.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed thoroughly with water
  5. customthen partially dried
  6. additionThe solid was added to 1:1 CH3CN—H2O (200 ml)
  7. filtrationsitrred then filtered
  8. washthe resulting yellow powder washed thoroughly with acetonitrile (500 ml×5)
  9. customthen dried under hi-vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-9599b8bfffbf4feeba657d23dc68960b
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232290B1

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