Methyl chloroformate → Methyl[2-(2-bromo-4-trifluoromethylphenyl)ethyl](1-propylbutyl)carbamate

HRID 387664Notes

Reaction equation

HRID 387664 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([O:31][CH3:32])=[O:30]>O1CCCC1>[CH3:32][O:31][C:29](=[O:30])[N:14]([CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=1[Br:1])[CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 68471227HCID 68471227, compound

Product 1

HCID 68474453Methyl[2-(2-bromo-4-trifluoromethylphenyl)ethyl](1-propylbutyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

770 mg of N-[2-(2-bromo-4-trifluoromethylphenyl)ethyl]heptan-4-amine in solution in 15 cm3 of anhydrous tetrahydrofuran and 500 mg of potassium carbonate are stirred under an inert atmosphere at a temperature in the vicinity of 5° C. 0.19 cm3 of methyl chloroformate is introduced over 5 minutes into the reaction mixture. The reaction mixture is brought to reflux over 15 h, the insoluble material is separated by filtration and the filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). The residual oil is purified by filtration through a silica pellet using a mixture of 10% ethyl acetate and 90% cyclohexane as eluent. The organic phase is then concentrated to dryness using a rotary evaporator under reduced pressure (5 kPa) in order to result in 666 mg of methyl[2-(2-bromo-4-trifluoromethylphenyl)ethyl](1-propylbutyl)carbamate in the form of a colorless oil.

Workup

  1. temperatureto reflux over 15 h
  2. customthe insoluble material is separated by filtration
  3. concentrationthe filtrate is concentrated
  4. customa rotary evaporator under reduced pressure (5 kPa)
  5. filtrationThe residual oil is purified by filtration through a silica
  6. additiona mixture of 10% ethyl acetate and 90% cyclohexane as eluent
  7. concentrationThe organic phase is then concentrated to dryness
  8. customa rotary evaporator under reduced pressure (5 kPa) in order
  9. customto result in 666 mg of methyl[2-(2-bromo-4-trifluoromethylphenyl)ethyl](1-propylbutyl)carbamate in the form of a colorless oil

Sources & evidence

ORD record
ord-6dfed22babad40118b03e06181e9b694
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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