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Pyridine → 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide

HRID 325728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 325728
[CH2:1]([N:8]1[C:12]([C:13](Cl)=[O:14])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C(C([O-])=O)=NN=N1)C1C=CC=CC=1.[K+].[CH3:32][C:33]1[CH:38]=[C:37]([C:39]([CH3:41])=[O:40])[C:36]([OH:42])=[C:35]([NH2:43])[CH:34]=1.N1C=CC=CC=1>C(Cl)Cl>[C:39]([C:37]1[C:36]([OH:42])=[C:35]([CH:34]=[C:33]([CH3:32])[CH:38]=1)[NH:43][C:13]([C:12]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][N:11]=1)=[O:14])(=[O:40])[CH3:41]
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 27564491-(3-Amino-2-hydroxy-5-methylphenyl)ethan-1-oneHCID 204638761-benzyl-1H-tetrazole-5-carbonyl chlorideHCID 23688251Potassium 1-Benzyl-1H-tetrazole-5-carboxylate

Produkt 1

HCID 1360453873'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of crude 1-benzyl-1H-tetrazole-5-carbonyl chloride (prepared from 0.73 g of potassium 1-benzyl-1H-tetrazole-5-carboxylate in the manner hereinbefore described in Reference Example 3) in dry methylene chloride (14 ml) was added to a stirred mixture of 3-amino-2-hydroxy-5-methylacetophenone (0.5 g) and pyridine (0.27 g) in dry methylene chloride (12 ml) at between 5° and 10° C. Stirring was maintained for 2 hours, allowing the temperature to rise to room temperature, and then the mixture was left to stand overnight. A further portion of methylene chloride (20 ml) was then added and the mixture was washed with water. The organic phase was dried over magnesium sulphate, and evaporated in vacuo to give a solid, which was recrystallised from ethanol, to give 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide (1.0 g), m.p. 183°-184° C.

Aufarbeitung

  1. temperaturewas maintained for 2 hours
  2. customto rise to room temperature
  3. waitthe mixture was left
  4. washthe mixture was washed with water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a solid, which
  8. customwas recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-546e0d984c62468d83cbb73e23c50502
Quelldatensatz
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04442115

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