Diisopropylamine → 3-Fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamide

HRID 1930827Notes

Reaction equation

HRID 1930827 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH:19]([NH:22][CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:22]([CH:23]([CH3:25])[CH3:24])[CH:19]([CH3:21])[CH3:20])=[O:7]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 24386Thionyl ChlorideHCID 5192223-Fluoro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 442031433-Fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamideYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 15.9 mmol 3-Fluoro-5-(Trifluoromethyl)benzoic acid in 20 ml toluene containing 2 drops of DMF was added 79.7 mmol thionylchloride at 0° C. The mixture was heated at 85° C. for 5 hours. The solvent was carefully removed in vacuo. The colorless liquid was dissolved in 25 ml dichloromethane and cooled to 0° C. 63.8 mmol diisopropylamine was added dropwise. The mixture was allowed to warm to RT. After 1 hour the solvent was removed in vacuo. The residue was taken in ethyl acetate and washed twice with water. The washings were extracted once with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow solid (85% yield). MS (m/e): 291.9 (M+, 100%)

Workup

  1. customThe solvent was carefully removed in vacuo
  2. dissolutionThe colorless liquid was dissolved in 25 ml dichloromethane
  3. temperaturecooled to 0° C
  4. temperatureto warm to RT
  5. customAfter 1 hour the solvent was removed in vacuo
  6. washwashed twice with water
  7. extractionThe washings were extracted once with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-dbbaccd497274d47b7e03cb0e803411c
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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