Bis-(1H-imidazol-2-YL)-methanone → HCID 19867717, compound

HRID 1198931Notes

Reaction equation

HRID 1198931 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[CH3:13][CH:14]1[C:23]2[C:18](=[C:19]([CH3:32])[CH:20]=[C:21]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH2:31])[CH:22]=2)[NH:17][C:16](=[O:33])[CH2:15]1>O1CCCC1>[CH3:13][CH:14]1[C:23]2[C:18](=[C:19]([CH3:32])[CH:20]=[C:21]([N:24]3[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[NH:31][C:1]3=[O:2])[CH:22]=2)[NH:17][C:16](=[O:33])[CH2:15]1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 19867712HCID 19867712, compound

Product 1

HCID 19867717HCID 19867717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of carbonyl diimidazole (0.33 g) in tetrahydrofuran (THF) (2 cm3) was added dropwise to a stirred solution of 3,4-dihydro-4,8-dimethyl-6-[(N-2-aminophenyl)amino]-2-(1H)-quinolone (0.24 g) in THF (2 cm3) at room temperature (20°). After 2 hours the solvent was evaporated in vacuo and the residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate. Collection and evaporation of appropriate fractions afforded a solid which was recrystallised from ethyl acetate to give the title compound, m.p. 250°-254° (0.13 g).

Workup

  1. customAfter 2 hours the solvent was evaporated in vacuo
  2. customthe residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  3. washeluting with ethyl acetate
  4. customCollection and evaporation of appropriate fractions
  5. customafforded a solid which
  6. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-941f5100aac64e1c980598f93a3da2c5
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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