Triethylamine → HCID 178473586, compound

HRID 1745844Notes

Reaction equation

HRID 1745844 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[C-:8]1(C(O)=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH-:16]1[CH:20]=[CH:19]C=C1.[Fe+2:21].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[NH:40][NH2:41]>ClCCl.C1(C)C=CC=CC=1>[C-:6]1([NH:3][C:4]([NH:41][NH:40][C:39]([O:43][CH2:44][CH3:45])=[O:42])=[O:14])[CH:7]=[CH:19][CH:20]=[CH:16]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 199401P,P-Diphenylphosphinic azideHCID 157642301271-42-7

Product 1

HCID 178473586HCID 178473586, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6344DichloromethaneSolvent2×

Procedure

Under ice cooling, 0.6 mL (4.3 mmols) of triethylamine was added to a mixture of 0.5 g (2.17 mmols) of ferrocenecarboxylic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 0.47 mL (2.17 mmols) of diphenylphosphorylazide and 4 mL of toluene and 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 0.34 g (3.27 mmols) of ethyl carbazate was added to the mixture while stirring at room temperature. The reaction mixture was heated under reflux for an hour and then 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 then concentrated under reduced pressure. The resulting residue was washed with a hexane-dichloromethane (1:1) mixture to give 0.52 g (72%) of ethyl 3-ferrocenylcarbamoylcarbazate as yellow powders.

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 reaction mixture was heated
  8. temperatureunder reflux for an hour
  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. washThe resulting residue was washed with a hexane-dichloromethane (1:1) mixture

Sources & evidence

ORD record
ord-9380620449da424c93e7c2188113f565
Source dataset
uspto-grants-2006_03
Patent number
US07019146B1

Reaction notes

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