Reaction #1747869

Reaction equation

4-iodobenzoyl chloride

o-aminodiphenylamine

ammonia

→

N-Phenyl-2-(4-iodophenyl)benzimidazole

Solvents

ethanol

Conditions

Workup

1. 1
   Otherformed from 85-90° C
2. 2
   Other(5 min)
3. 3
   TemperatureAfter cooling
4. 4
   FiltrationThe precipitate was filtered off with suction
5. 5
   Washwashed with ethanol
6. 6
   workup.STIRRINGstirred up again in 400 ml of ethanol
7. 7
   Otherwhich formed a solution which
8. 8
   TemperatureAfter cooling to 5-10° C.
9. 9
   Filtrationthe precipitate was filtered off with suction
10. 10
    Washwashed with cold ethanol
11. 11
    Otherdried at 75° C. in a vacuum
12. 12
    Otherdrying cabinet
13. 13
    Otherwere obtained

Procedure

37.47 g (136 mmol) of 97% 4-iodobenzoyl chloride and 12.82 g (68.2 mmol) of 98% o-aminodiphenylamine were heated to 100° C., in the course of which a stirrable melt formed from 85-90° C. Once the gas evolution had ended (5 min), the melt solidified. The reaction mixture was kept at 100° C. for another 3 hours. After cooling, it was admixed with 100 ml of ethanol with stirring. The precipitate was filtered off with suction, washed with ethanol and stirred up again in 400 ml of ethanol. The suspension was heated to 75° C., which formed a solution which was adjusted to pH 8 with 29 ml of 25% ammonia. After cooling to 5-10° C., the precipitate was filtered off with suction, washed with cold ethanol and dried at 75° C. in a vacuum drying cabinet. 18.37 g (68% of theory) of light gray microcrystals having an m.p. of 178-181° C. were obtained.

Source