N,N'-Dimethylethylenediamine → HCID 58829446, compound

HRID 2115895Notes

Reaction equation

HRID 2115895 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6](Br)[CH:7]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 58829446HCID 58829446, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Into a 16 by 100 mm vial sparged with argon was added 3-amino-5-bromobenzotrifluoride (1 g, 4.16 mmol), 2-pyrrolidinone (425 mg, 5 mmol), N,N′-dimethylethylenediamine (37 mg, 0.416 mmol), potassium carbonate (1.15 g, 8.33 mmol), copper(1)iodide (80 mg, 0.416 mmol), and toluene (1 mL). Vial capped, heated with stirring at 85° C. for 24 h. Reaction cooled to RT, solvent removed under reduced pressure, reconstituted in DCM and filtered through silica. Affords a gray solid. MS m/z=245 [M+H]+. Calc'd for C11H11F3N2O: 244.2

Workup

  1. customInto a 16 by 100 mm vial sparged with argon
  2. customVial capped
  3. temperatureheated
  4. customReaction
  5. temperaturecooled to RT
  6. customsolvent removed under reduced pressure
  7. filtrationfiltered through silica
  8. customAffords a gray solid

Sources & evidence

ORD record
ord-ce3fb6620f15460c9a8770d00fba3248
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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