Aniline → HCID 12273390, compound

HRID 1973409Notes

Reaction equation

HRID 1973409 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[N:10]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1>CCOCC>[C:2]1([NH:1][C:9]2[N:10]=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 12273384HCID 12273384, compound

Product 1

HCID 12273390HCID 12273390, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

11.2 g (0.12 mol) of aniline are added dropwise, whilst stirring, to 8.7 g (0.03 mol) of 2,4-dichloro-4,5-diphenyl-4H-imidazole in 150 ml of ether. The mixture was then stirred for 20 hours at room temperature. The precipitate produced was filtered off and dried. After adding methylene chloride, the solution was repeatedly washed with water and then dried over sodium sulphate, and the solvent was distilled off. The oily residue crystallised on addition of a little ether. The product obtained was recrystallised from benzene/petroleum ether. 5.2 g (44% of theory) of 2,4-diphenylamino-4,5-diphenyl-4H-imidazole of melting point 153° - 156° C were obtained.

Workup

  1. customThe precipitate produced
  2. filtrationwas filtered off
  3. customdried
  4. additionAfter adding methylene chloride
  5. washthe solution was repeatedly washed with water
  6. dry with materialdried over sodium sulphate
  7. distillationthe solvent was distilled off
  8. customThe oily residue crystallised on addition of a little ether
  9. customThe product obtained
  10. customwas recrystallised from benzene/petroleum ether

Sources & evidence

ORD record
ord-cec3f6a833444bc482c65d9009f46d2d
Source dataset
uspto-grants-1976_12
Patent number
US03997552

Reaction notes

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