2-Methylimidazole → HCID 68454783, compound

HRID 2357425Notes

Reaction equation

HRID 2357425 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C(=O)C)=[C:15]([O:23][CH3:24])[CH:14]=2)C(O)=O)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC1NC=CN=1>C(O)COCCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:23][CH3:24])[CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 516892Sodium BicarbonateHCID 86618677HCID 86618677, compound

Product 1

HCID 68454783HCID 68454783, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A mixture of α-(4′-chlorophenyl)-4-acetyloxy-3-methoxy cinnamic acid (0.0083 mol), NaHCO3 (10%, 5 mL) and methylimidazole (2 mL) and diethylene glycol (8 mL) were taken in a 100 ml round bottom flask fitted with a condenser. The flask was shaken well and placed inside the microwave oven and irradiated (200 W, 180° C.) for 9 minutes in parts. After completion of reaction, the reaction mixture was worked (yield 89%) as in example I; solid, (m.p. 121-124° C.); 1H NMR (CDCl3) δ 7.35 (2H, d, J=8.48 Hz), 7.25 (2H, d, J=8.07 Hz), 6.96 (3H, m), 6.87 (2H, d, J=8.07 Hz), 5.72 (1H, s), 3.87 (3H, s); 13C NMR (CDCl3) δ 146.8, 145.8, 136.1, 132.7, 129.6, 129.2, 128.8, 127.4, 125.1, 120.6, 114.6, 108.3 and 55.9. HREIMS data: m/z [M+H]+ for C15H14O2Cl, calculated=261.7229; observed=261.7228.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted with a condenser
  3. customirradiated (200 W, 180° C.) for 9 minutes in parts
  4. customAfter completion of reaction

Sources & evidence

ORD record
ord-0fc1fb90029c462eb035f00fbdb35ff4
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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