Toluene → HCID 22625918, compound

HRID 277779Notes

Reaction equation

HRID 277779 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:30](Cl)(Cl)=[O:31].C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]=[C:30]=[O:31])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 88675Proton spongeHCID 104223Phenethylamine, m-trifluoromethyl-

Product 1

HCID 22625918HCID 22625918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a methylene chloride solution of commercially available 2-(3-trifluoromethylphenyl)ethylamine (5.65 mmol) at 0° C. was added solid Proton sponge (5.65 mmol) then a 20% solution of phosgene in toluene (5.65 mmol). The solution was stirred at 25° C. for 1 hour and then washed with 1N HCl (40 mL). The methylene chloride was then dried with sodium sulfate and evaporated. 1H-NMR (CDCl3): 7.5 ppm (m, 4H); 3.6 ppm (t, 2H); 2.95 ppm (t, 2H).

Workup

  1. washwashed with 1N HCl (40 mL)
  2. dry with materialThe methylene chloride was then dried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-14752c278bc741549bd1462504deb75d
Source dataset
uspto-grants-2002_03
Patent number
US06358956B1

Reaction notes

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