Ammonia → 2-(4-Iodophenyl)-1-phenyl-1H-benzimidazole

HRID 1660687Notes

Reaction equation

HRID 1660687 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.[CH:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.N>C(O)C>[C:14]1([N:17]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[N:24]=[C:6]2[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 68297N-Phenyl-o-phenylenediamineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 230940682-(4-Iodophenyl)-1-phenyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

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.

Workup

  1. customformed from 85-90° C
  2. custom(5 min)
  3. temperatureAfter cooling
  4. filtrationThe precipitate was filtered off with suction
  5. washwashed with ethanol
  6. stirringstirred up again in 400 ml of ethanol
  7. customwhich formed a solution which
  8. temperatureAfter cooling to 5-10° C.
  9. filtrationthe precipitate was filtered off with suction
  10. washwashed with cold ethanol
  11. customdried at 75° C. in a vacuum
  12. customdrying cabinet
  13. customwere obtained

Sources & evidence

ORD record
ord-d0d31b70ad7a4accb9f5af027c1b4417
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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