Toluene → HCID 86635501, compound

HRID 2198343Notes

Reaction equation

HRID 2198343 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[CH2:11](Br)[C:12]#[CH:13].C1(C)C=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:13][C:12]#[CH:11])[NH2:10])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 7842Propargyl bromideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 86635501HCID 86635501, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chlorophenylhydrazine hydrochloride (550 mg, 3 mmol) was added to a vigorously stirred mixture of tetra-n-butylammonium chloride (42 mg, 0.15 mmol) in 50% aqueous sodium hydroxide (3 mL) followed by 80% propargyl bromide in toluene (490 mg, 3.3 mmol). The reaction was stirred at room temperature for 20 h. The reaction was diluted with water (30 mL) and extracted with chloroform (3×10 mL). The combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to a dark brown oil (530 mg). The oil was subjected to column chromatography (silica gel, eluent: 50% dichloromethane in hexanes) to give an orange solid (260 mg, 48%).

Workup

  1. extractionextracted with chloroform (3×10 mL)
  2. dry with materialThe combined organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a dark brown oil (530 mg)

Sources & evidence

ORD record
ord-869e98ed0bdf41329503068bc6c20e37
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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