1H-1,2,4-Triazole → HCID 20273714, compound

HRID 371313Notes

Reaction equation

HRID 371313 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[CH2:8]([Si:11]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH:12](Cl)[CH3:13])[CH:9]=[CH2:10].C([Si](C1C=CC(F)=CC=1)(C1C=CC(F)=CC=1)CCCl)C=C>CN(C)C=O.O.ClCCl.CC(C)=O>[CH2:8]([Si:11]([C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH:12]([N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[CH3:13])[CH:9]=[CH2:10]

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 13489945HCID 13489945, compoundHCID 20273720HCID 20273720, compound

Product 1

HCID 20273714HCID 20273714, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

A mixture of 1.78 g (37 mmol) of 50% sodium hydride, 30 ml of dimethylformamide, and 2.56 g (37 mmol) of 1H-1,2,4-triazole is stirred at 50° for one hour, and a solution of 10 g (33.7 mmol) of a 1:1 mixture of allyl[bis(4-fluorophenyl)]-1-chloroethylsilane and allyl[bis(4-fluorophenyl)]-2-chloroethylsilane in 10 ml of dimethylformamide is added. The mixture is stirred at 50° for 64 hours, cooled, diluted with water, and extracted with ether. The ether extracts are washed with water and brine, dried over sodium sulfate, and evaporated to leave a viscous oil. Chromatography over silica gel eluting with 4:1 dichloromethane-acetone provides the title compound.

Workup

  1. additionis added
  2. stirringThe mixture is stirred at 50° for 64 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. washThe ether extracts are washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto leave a viscous oil

Sources & evidence

ORD record
ord-771fb5623fc94443b00e70f373588b9c
Source dataset
uspto-grants-1985_07
Patent number
US04530922

Reaction notes

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