1,2-Dichloroethane → HCID 848829, compound

HRID 1896219Notes

Reaction equation

HRID 1896219 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.[C:23]([CH2:31][CH2:32][C:33](O)=[O:34])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>O1CCOCC1>[O:30]=[C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:31][CH2:32][C:33]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[O:34]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7813p-ToluidineHCID 8471TriethylamineHCID 728713-Benzoylpropionic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 848829HCID 848829, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

EDC (347 mg, 1.81 mmol) and HOBT (254 mg, 1.88 mmol) were added to mixture of p-toluidine (129 mg, 1.20 mmol) and 3-benzoylpropionic acid 27 (218 mg, 1.21 mmol) in 1,4-dioxane (3 mL) at room temperature. It was stirred for 20 minutes and then added triethylamine (0.5 mL, 3.59 mmol). The reaction mixture was stirred for 20 h at room temperature and the solvent was evaporated under vacuum. The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1) yielded the compound 28 (252 mg, 78%). 1H-NMR (CDCl3, 300 MHz) δ 2.30 (s, 3H), 2.80 (t, J=6.3 Hz, 2H), 3.45 (t, J=6.3 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.4 Hz, 2H), 7.47 (m, 2H), 7.58 (m, 1H), 7.99 (m, 1H).

Workup

  1. stirringThe reaction mixture was stirred for 20 h at room temperature
  2. customthe solvent was evaporated under vacuum
  3. customThe residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-02e72c2d45214cb68ed53f3da54b274e
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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