Diisopropylethylamine → HCID 58622888, compound

HRID 1269641Notes

Reaction equation

HRID 1269641 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[NH:5][CH2:6][CH2:7][CH2:8][CH3:9].Br[CH2:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N:5]([CH2:15][C:16]2[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=2)[CH2:6][CH2:7][CH2:8][CH3:9])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18448358HCID 18448358, compoundHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622888HCID 58622888, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-N-butyl-2-methylaniline (700 mg, 2.89 mmol) in dry acetonitrile (75 mL) was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (830 mg, 2.89 mmol) and N,N-diisopropylethylamine (331 μL, 1.9 mmol). The resultant mixture was heated at 80° C. for 3 h. The reaction mixture was cooled and the solvents removed in vacuo, diluted with water (50 mL) and extracted with CH2Cl2 (2×100 mL). The organic solution was dried (Na2SO4) and the solvents removed in vacuo. Purification by SPE (silica, 20 g) eluted with 100:2 to 100:5 cylclohexane:EtOAc afforded the title compound as a colourless oil (749 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvents removed in vacuo
  3. additiondiluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×100 mL)
  5. dry with materialThe organic solution was dried (Na2SO4)
  6. customthe solvents removed in vacuo
  7. customPurification by SPE (silica, 20 g)
  8. washeluted with 100:2 to 100:5 cylclohexane

Sources & evidence

ORD record
ord-8fb370debc874f3b94653c8d1f984661
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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