Water → Methyl [2-amino-5-(trifluoromethyl)benzyl][3,5-bis(trifluoromethyl)benzyl]carbamate

HRID 217478

Reaction equation

HRID 217478 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=1.CN1CCOCC1.Cl[C:37]([O:39][CH3:40])=[O:38].O>COCCOC.CCCCCC.[Hg]>[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:3]=1[CH2:4][N:5]([CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[C:9]([C:17]([F:18])([F:19])[F:20])[CH:8]=1)[C:37](=[O:38])[O:39][CH3:40]

Participants

8

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 59343853[2-Amino-5-(trifluoromethyl)benzyl][3,5-bis(trifluoromethyl)benzyl]amine

Product 1

HCID 59343867Methyl [2-amino-5-(trifluoromethyl)benzyl][3,5-bis(trifluoromethyl)benzyl]carbamate

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 250-mL flask equipped with a septum inlet, magnetic stirring bar, and connecting tube leading to a mercury bubbler was placed 12 g (0.029 mol) of [2-amino-5-(trifluoromethyl)benzyl][3,5-bis(trifluoromethyl)benzyl]amine in 120 mL DME. To the reaction flask with stirring was added 6.4 mL (0.058 mol) N-methylmorpholine and the mixture was cooled in an ice bath under nitrogen. To this mixture was added dropwise over ten minutes, 2.7 mL (0.035 mol) of methyl chloroformate. Afterwards, the mixture was allowed to stir for 15 minutes and HPLC showed no starting material present. Water was added to the mixture and the contents were diluted with hexane and transferred to a separatory funnel. The layers were separated, then washed with brine, dried over magnesium sulfate, filtered and concentrated to give 13 g crude oil. The oil was chromatographed on a Biotage 40M cartridge with methylene chloride/hexane to give methyl [2-amino-5-(trifluoromethyl)benzyl][3,5-bis(trifluoromethyl)benzyl]carbamate as a yellow oil.

Workup

  1. customIn a 250-mL flask equipped with a septum inlet, magnetic stirring bar
  2. temperaturethe mixture was cooled in an ice bath under nitrogen
  3. additionTo this mixture was added dropwise over ten minutes
  4. stirringto stir for 15 minutes
  5. customtransferred to a separatory funnel
  6. customThe layers were separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give 13 g crude oil
  12. customThe oil was chromatographed on a Biotage 40M cartridge with methylene chloride/hexane

Sources & evidence

ORD record
ord-0b582c3edee94405939c323c6420000a
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Linked notes

Loading…