Ethyl Acetate → HCID 18393043, compound

HRID 1739515Notes

Reaction equation

HRID 1739515 reaction equation
[C:1]1([C:7]2[N:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:21]([C:23]1[S:27][C:26](=[N:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[N:25]([CH2:35][C:36]2[CH:41]=[CH:40][C:39](I)=[CH:38][CH:37]=2)[N:24]=1)[CH3:22].C(OCC)(=O)C>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[C:12]([N:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[C:39]2[CH:40]=[CH:41][C:36]([CH2:35][N:25]3[N:24]=[C:23]([CH2:21][CH3:22])[S:27][C:26]3=[N:28][C:29](=[O:34])[C:30]([F:31])([F:33])[F:32])=[CH:37][CH:38]=2)=[N:8][N:9]=[N:10]1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10899692HCID 10899692, compoundHCID 18393045HCID 18393045, compoundHCID 178418339Butyllithium

Product 1

HCID 18393043HCID 18393043, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 5-phenyl-1-tert-butyl-1H-tetrazole (1.0 g) in tetrahydrofuran (20 ml) was added dropwise n-butyl lithium (1.6M hexane solution, 3.5 ml) keeping the temperature below -20° C., followed by stirring at -5° C. for one hour. Zinc chloride (1.0M diethyl ether solution, 6.0 ml) was added dropwise to the reaction mixture keeping the temperature below -30° C., followed by stirring at room temperature for 2 hours. To the resulting mixture were added 5-ethyl-3-(4-iodobenzyl)-2-trifluoroacetylimino-1,3,4-thiadiazoline (1.2 g) and tetrakis(triphenyl-phosphine)palladium (100 mg), and they were heated under reflux overnight. Ethyl acetate (100 ml) was added to the reaction mixture, and the resulting mixture was washed with 10% aqueous citric acid solution and dried over anhydrous magnesium sulfate, followed by removal through distillation. The residue so obtained was separated by column chromatography on silica gel, whereby 830 mg of the title compound was obtained in the oily form.

Workup

  1. customthe temperature below -20° C.
  2. customthe temperature below -30° C.
  3. stirringby stirring at room temperature for 2 hours
  4. temperaturewere heated
  5. temperatureunder reflux overnight
  6. washthe resulting mixture was washed with 10% aqueous citric acid solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customfollowed by removal through distillation
  9. customThe residue so obtained
  10. customwas separated by column chromatography on silica gel

Sources & evidence

ORD record
ord-e1ef3ab9cda3411bbdcc3be2291fc97d
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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