Toluene → HCID 86743764, compound

HRID 1199599Notes

Reaction equation

HRID 1199599 reaction equation
ClC1C=CC(N)=C([F:9])C=1.ClC([O:13][C:14](Cl)(Cl)Cl)=O.[ClH:18].[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH2:24])[CH3:20].C([N:28]([CH2:31][CH3:32])CC)C.[C:33]1([CH3:39])C=CC=[CH:35][CH:34]=1>C(Cl)(Cl)Cl.CCCCCCC.O>[Cl:18][C:33]1[CH:39]=[CH:32][C:31]([NH:28][C:14]([NH:24][CH:23]([F:9])[C:22]([O:21][CH2:19][CH3:20])=[O:25])=[O:13])=[CH:35][CH:34]=1

Participants

9

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 10426DiphosgeneHCID 938984-Chloro-2-fluoroanilineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 86743764HCID 86743764, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8900HeptaneSolvent

Procedure

To a stirred solution of 20.0 g (0.137 mole) of 4-chloro-2-fluoroaniline in 300 mL of toluene was slowly added 16.2 g (0.082 mole) of trichloromethyl chloroformate. The reaction mixture was heated at reflux for approximately 18 hours. The mixture was cooled, and the solvent was removed by distillation under reduced pressure leaving an oil. The oil was dissolved in 100 mL of chloroform, and 20.6 g (0.15 mole) of glycine ethyl ester hydrochloride was added. Triethylamine (15.2 g, 0.15 mole) was added slowly, and the resultant mixture was stirred at room temperature for two hours. The reaction mixture was diluted with 300 mL of n-heptane and 100 mL of water, causing a precipitate to form. The precipitate was collected by filtration to give 36.4 g of ethyl 4-chloro-2-fluorophenylaminocarbonylaminoacetate, m.p. 125°-129° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by distillation under reduced pressure
  5. customleaving an oil
  6. customto form
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-090fe35299ce4bec84cc2eab37e08e2e
Source dataset
uspto-grants-1990_02
Patent number
US04902338

Reaction notes

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