4-Tert-Butylaniline → Methyl 4-{[(4-tert-butylphenyl)amino]carbonyl}benzoate

HRID 736384Notes

Reaction equation

HRID 736384 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.[C:14]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>O=S(Cl)Cl>[C:14]([C:18]1[CH:19]=[CH:20][C:21]([NH:22][C:6]([C:5]2[CH:4]=[CH:3][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:10][CH:9]=2)=[O:8])=[CH:23][CH:24]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 7913868Methyl 4-{[(4-tert-butylphenyl)amino]carbonyl}benzoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

mono-Methyl terephthalate (1.02 g, 5.67 mmol) was refluxed in SOCl2 (10 mL) for 1 hour, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was taken up in tetrahydrofuran (30 mL) and treated with 4-tert-butylaniline (0.9 mL, 5.65 mmol) and DIEA (5 mL, 28.8 mmol) at room temperature. After stirring overnight, the mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate. The ethyl acetate was washed with H2O and brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with 3:2 hexanes:ethyl acetate and the solid air-dried to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.37 (s, 1H), 8.08 (m, 4H), 7.69 (m, 2H), 7.39 (m, 2H), 3.90 (s, 3H), 1.29 (s, 9H); MS (ESI+) m/z 312 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationthe mixture was concentrated under reduced pressure
  3. washThe ethyl acetate was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was triturated with 3:2 hexanes
  8. dry with materialethyl acetate and the solid air-dried

Sources & evidence

ORD record
ord-5024a156ffc542d3b9b958f352f5729c
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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