Sodium Carbonate → HCID 53818166, compound

HRID 962806Notes

Reaction equation

HRID 962806 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1([C:9]([OH:25])([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:10][C:11]([Cl:18])=[C:12]([Cl:17])[C:13](O)([CH3:15])[CH3:14])[CH2:8][CH2:7]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Cl:5][C:6]1([C:9]([OH:25])([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:10][C:11]([Cl:18])=[C:12]([Cl:17])[C:13]([CH3:15])=[CH2:14])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 54514415HCID 54514415, compound

Product 1

HCID 53818166HCID 53818166, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.71 g (6 mmol) of thionyl chloride are added at room temperature with stirring to a mixture of 1.77 g (5 mmol) of 6-(1-chlorocyclopropyl)-3,4-dichloro-2,6-dihydroxy-2-methyl-7-(1,2,4-triazol-1-yl)-hept-3-ene and 20 ml of methylene chloride, and the mixture is then heated at reflux for 5 hours. Aqueous sodium carbonate solution is subsequently added to the reaction mixture, which is then subjected several times to extraction with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The product which remains is chromatographed over silica gel using ethyl acetate. Concentration of the eluate gives 0.5 g (20% of theory) of 6(1-chlorocyclopropyl)-3,4dichloro-6-hydroxy-2-methyl-7-(1,2,4-triazol-1-yl)hepta-1,3-diene in the form of a colourless oil.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureat reflux for 5 hours
  3. extractionto extraction with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe product which remains is chromatographed over silica gel

Sources & evidence

ORD record
ord-693d531fc60640ab938eae538133088a
Source dataset
uspto-grants-1998_06
Patent number
US05760067

Reaction notes

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