Diisopropylamine → 4-Bromo-N,N-diisopropylbenzamide

HRID 2192999Notes

Reaction equation

HRID 2192999 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:21]([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 114644-Bromobenzoic acid

Product 1

HCID 36169884-Bromo-N,N-diisopropylbenzamide

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 4-bromobenzoic acid (200 g, 1 mol) and thionyl chloride (300 mL) was refluxed for 3 hours. The mixture was concentrated in vacuo to remove excessive thionyl chloride, and then azeotroped with toluene (3×). The crude residue was dissolved in CH2Cl2 (2 L) and cooled in ice-water bath. To the resulting solution was added dropwise a mixture of triethylamine (330 mL, 2.38 mol) and diisopropylamine (168 mL, 1.19 mol) over 1 hour. The solution was allowed to stir overnight, and then washed with 1N HCl, followed by brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-bromo-N,N-diisopropylbenzamide. LRMS calc'd for (C13H18BrNO) [M+H]+, 284; found 284.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove excessive thionyl chloride
  4. customazeotroped with toluene (3×)
  5. dissolutionThe crude residue was dissolved in CH2Cl2 (2 L)
  6. temperaturecooled in ice-water bath
  7. additionTo the resulting solution was added dropwise
  8. washwashed with 1N HCl
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2f6e77f14deb485d824e0b1ee25a082b
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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