Methanesulfonyl chloride → HCID 178425305, Verbindung

HRID 21659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21659
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CS(Cl)(=O)=O.[C:14]([N:18]([C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH2:19])([CH3:17])([CH3:16])[CH3:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CC(C)=O.C(N(CC)CC)C>[C:14]([N:18]([C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH:19][C:6]([C:4]1[N:3]=[N:2][NH:1][CH:5]=1)=[O:8])([CH3:17])([CH3:16])[CH3:15]

Komponenten

8

Edukt 4

HCID 31297Methanesulfonyl chlorideHCID 1401204-Carboxy-1,2,3-triazoleHCID 516892Sodium BicarbonateHCID 15452040N'-t-butyl-N'-(3-methylbenzoyl)hydrazine

Produkt 1

HCID 178425305HCID 178425305, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1,2,3-triazole-4-carboxylic acid (1.0 g) and triethylamine (0.9 g) were dissolved in 40 ml methylene chloride and cooled in an ice bath. Methanesulfonylchloride (1.0 g) was added dropwise. After addition was complete, the reaction mixture was stirred for 0.5 hours. N'-t-butyl-N'-(3-methylbenzoyl)hydrazine (1.84 g) in 10 ml CH2Cl2 was added dropwise. The resulting mixture was allowed to stand for 14 hours. Aqueous sodium bicarbonate was added. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow oil. Chromatography on silica gel using acetone as eluant afforded N'-t-butyl-N-1,2,3-triazole-4-carbonyl-N'-(3-methylbenzoyl)hydrazine.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. waitto stand for 14 hours
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-dffaf8d25a7f4b579f3a263f31bda5e4
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424333

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