Toluene → HCID 178473587, compound

HRID 1745843Notes

Reaction equation

HRID 1745843 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[C-:8]1(CC(O)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH-:17]1[CH:21]=[CH:20][CH:19]=C1.[Fe+2:22].C1(C)C=CC=CC=1.[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[NH:31][NH2:32]>ClCCl>[C-:7]1([CH2:6][NH:3][C:4]([NH:32][NH:31][C:30]([O:34][CH2:35][CH3:36])=[O:33])=[O:15])[CH:19]=[CH:20][CH:21]=[CH:17]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:22]

Participants

6

Reactant 4

HCID 1140Toluene3×HCID 8471TriethylamineHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 157685011287-16-7

Product 1

HCID 178473587HCID 178473587, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under ice cooling, 0.57 mL (4 mmols) of triethylamine was added to a mixture of 0.5 g (2 mmols) of ferroceneacetic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 0.44 mL (2 mmols) of diphenylphosphyrylazide and 4 mL of toluene. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with dichloromethane. The dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the organic layer was filtered and concentrated under reduced pressure to give 4 mL of the toluene solution. To the toluene solution obtained, 2 mL of toluene was added and 0.32 g (3 mmols) of ethyl carbazate was added to the mixture while stirring at room temperature. The mixture was then heated under reflux for 3 hours and diluted with dichloromethane. The dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the organic layer was filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 0.55 g (78%) of ethyl 3-(ferrocenylmethyl)carbamoylcarbazate as a yellow oily substance.

Workup

  1. washThe dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationthe organic layer was filtered
  4. concentrationconcentrated under reduced pressure
  5. customto give 4 mL of the toluene solution
  6. stirringwhile stirring at room temperature
  7. temperatureThe mixture was then heated
  8. temperatureunder reflux for 3 hours
  9. washThe dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution
  10. dry with materialAfter drying over anhydrous magnesium sulfate
  11. filtrationthe organic layer was filtered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-d7d696769c6e41069373ecec91119e9d
Source dataset
uspto-grants-2006_03
Patent number
US07019146B1

Reaction notes

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