Sodium Carbonate → HCID 10471556, compound

HRID 1003503Notes

Reaction equation

HRID 1003503 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:14]([NH2:24])[C:15]1[CH:23]=[CH:22][C:21]2[O:20][CH2:19][O:18][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[CH2:19]1[O:20][C:21]2[CH:22]=[CH:23][C:15]([CH2:14][NH:24][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:16][C:17]=2[O:18]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 103758454-Chloro-6-(methylthio)quinazoline

Product 1

HCID 10471556HCID 10471556, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.12 g(0.0196 mol) of 4-chloro-6-methylthioquinazoline, 3.70 g (0.0245 mol) of piperonylamine and 3.50 g (0.0330 mol) of sodium carbonate were mixed with 100 ml of isopropyl alcohol. The obtained mixture was heated under reflux for 24 hours and distilled under a reduced pressure to remove the solvent. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) and recrystallized from chloroform/n-hexane to give 5.32 g of the title compound as a pale-yellow crystal. molecular formula; C17H15O2N3S; yield(%); 83; m.p.(° C.); 174~175; Mass; 326 (M+H)+ ; NMR δ (CDCl3); 2.59 (3H, s), 4.79 (2H, d, J=5.6 Hz), 5.93 (2H, s), 6.77 (1H, d, J=8.0 Hz), 6.89 (1H, d, J=8.0 Hz), 6.94 (1H, s), 7.62 (1H, dd, J=8.8 Hz, 2.0 Hz), 7.75 (1H, d, J=8.8 Hz), 7.97 (1H, d, J=2.0 Hz), 8.10 (1H, brs), 8.56 (1H, s).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 24 hours
  3. distillationdistilled under a reduced pressure
  4. customto remove the solvent
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  6. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-cac3e70215d14f228b804fe78e6b3ce7
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

Loading…