Cyanuric chloride → Methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoate

HRID 1023704Notes

Reaction equation

HRID 1023704 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.C(N(CC)CC)C.[NH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1>CC(C)=O.CN(C)C1C=CN=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=2)=[O:14])[O:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7954Cyanuric chlorideHCID 8471TriethylamineHCID 12082Methyl 4-aminobenzoateHCID 584205144,5-Diisopropylfuran-2-carboxylic acid

Product 1

HCID 67395533Methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoateYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

A solution of 4,5-diisopropylfuran-2-carboxylic acid (50 mg, 0.255 mmol) and cyanuric chloride (71 mg, 0.385 mmol) in acetone (3 ml) was added with triethylamine (142 μl, 1.021 mmol), and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added with methyl 4-aminobenzoate (77 mg, 0.510 mmol), and the mixture was further stirred for 14 hours. The reaction solvent was evaporated, then the residue was dissolved in pyridine (1 ml), the solution was added with 4-dimethylaminopyridine (1 mg, 8.20 μmol), and the mixture was stirred at room temperature for 4 hours. Pyridine was evaporated, and then the reaction mixture was dissolved in 10% methanol-chloroform, the solution was added with silica gel (1.0 g), and the mixture was evaporated to dryness. The residue was purified by silica gel chromatography [hexane-ethyl acetate (6:1)] to obtain methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoate (75 mg, 89%) as colorless prisms.

Workup

  1. stirringthe mixture was further stirred for 14 hours
  2. customThe reaction solvent was evaporated
  3. dissolutionthe residue was dissolved in pyridine (1 ml)
  4. stirringthe mixture was stirred at room temperature for 4 hours
  5. customPyridine was evaporated
  6. dissolutionthe reaction mixture was dissolved in 10% methanol-chloroform
  7. additionthe solution was added with silica gel (1.0 g)
  8. customthe mixture was evaporated to dryness
  9. customThe residue was purified by silica gel chromatography [hexane-ethyl acetate (6:1)]

Sources & evidence

ORD record
ord-a939961a1e2345c4ad57a37bd8d47e01
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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