Methane → Fvmdvjbtjhltex-uhfffaoysa-

HRID 918193Notes

Reaction equation

HRID 918193 reaction equation
I.CS[C:4]1[NH:5][CH2:6][CH2:7][N:8]=1.[F:9][C:10]1[CH:28]=[CH:27][C:13]([CH2:14][N:15]2C(=O)O[C:18](=[O:19])[C:17]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:16]23)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C>C(O)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:16]3[C:17](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:18](=[O:19])[N:5]3[CH2:6][CH2:7][N:8]=[C:4]23)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 10340Sodium CarbonateHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)HCID 12223278N-(p-fluorobenzyl)isatoic anhydride

Product 1

HCID 4413845Fvmdvjbtjhltex-uhfffaoysa-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A charge of 26 kgs. toluene, 2.5 kgs. 2-methylmercaptoimidazoline hydroiodide, 2.4 kgs. N-(p-fluorobenzyl)isatoic anhydride and 1.55 kgs. powdered anhydrous sodium carbonate is refluxed for 18 - 20 hours in a reaction vessel which is vented to a caustic gas washing tower. Any water formed during the reaction is collected in a Dean-Stark separator. The reaction is cooled to 20°C. and 10 kgs. water added. The mixture is stirred for about 30 minutes and the solids collected, washed several times with 2 kg. portions of water, and three times with 0.8 kg. toluene. The solids are then dried at reduced pressure (about 55°C.) to obtain a crude product, m.p. 196°-198°C. The crude is dissolved at 50°C. in a solution of 14 kgs. chloroform and 4 kgs. ethanol and treated in solution with 0.1 kg. decoloring charcoal for about 10 minutes. The charcoal is removed by filtration through a celite bed and solids reprecipitated by concentrating the filtrate to a volume of about 8 liters. This concentrate is cooled to 0°-5°C., the solids collected by filtration, washed with cold ethanol and then diethyl ether, and dried at reduced pressure to obtain 10-(4'-fluorobenzyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one, m.p. 197°-198°C.

Workup

  1. washwashing tower
  2. customAny water formed during the reaction
  3. customis collected in a Dean-Stark separator
  4. additionwater added
  5. customthe solids collected
  6. washwashed several times with 2 kg
  7. customThe solids are then dried at reduced pressure (about 55°C.)
  8. customto obtain a crude product, m.p. 196°-198°C
  9. customThe charcoal is removed by filtration through a celite bed and solids
  10. customreprecipitated
  11. concentrationby concentrating the filtrate to a volume of about 8 liters
  12. temperatureThis concentrate is cooled to 0°-5°C.
  13. filtrationthe solids collected by filtration
  14. washwashed with cold ethanol
  15. dry with materialdiethyl ether, and dried at reduced pressure

Sources & evidence

ORD record
ord-871bbab71cb7422090bb138c7790c00d
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

Loading…