Ethyl Acetate → HCID 15263683, compound

HRID 1739514Notes

Reaction equation

HRID 1739514 reaction equation
[C:1]1([C:7]2[N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.I[C:37]1[CH:57]=[CH:56][C:40]([CH2:41][N:42]2[N:46]=[C:45]([CH2:47][CH3:48])[S:44][C:43]2=[N:49][C:50](=[O:55])[C:51]([F:54])([F:53])[F:52])=[CH:39][CH:38]=1.C(OCC)(=O)C>O1CCCC1.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:47]([C:45]1[S:44][C:43](=[N:49][C:50](=[O:55])[C:51]([F:53])([F:52])[F:54])[N:42]([CH2:41][C:40]2[CH:39]=[CH:38][C:37]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:7]3[N:11]([C:12]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:10]=[N:9][N:8]=3)=[CH:57][CH:56]=2)[N:46]=1)[CH3:48]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 104303585-phenyl-1-trityl-1H-tetrazoleHCID 18393045HCID 18393045, compoundHCID 178418339Butyllithium

Product 1

HCID 15263683HCID 15263683, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 5-phenyl-1-triphenylmethyl-1H-tetrazole (2.3 g) in tetrahydrofuran (20 ml) was added dropwise n-butyl lithium (1.6M hexane solution, 4.0 ml) keeping the temperature below -20° C., followed by stirring at -5° C. for one hour. Zinc chloride (1.0M diethyl ether solution, 7.0 ml) was added dropwise keeping the temperature below -30° C., followed by stirring at room temperature for two hours. To the reaction mixture, 3-(4-iodobenzyl)-5-ethyl-2-trifluoroacetylimino-1,3,4-thiadiazoline (1.4 g) and tetrakis(triphenylphosphine)-palladium (100 mg) were added, followed by heating under reflux overnight. After ethyl acetate (50 ml) was added to the reaction mixture, 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.

Workup

  1. customthe temperature below -20° C.
  2. customthe temperature below -30° C.
  3. stirringby stirring at room temperature for two hours
  4. temperatureby heating
  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-ac75fc893f634fb5857b739eb73a207e
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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