HCID 12282158, compound → HCID 178509632, compound

HRID 1167288Notes

Reaction equation

HRID 1167288 reaction equation
[NH2:1][CH:2]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH:3]([NH2:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.Cl.[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([C:26](=N)OCC)=[CH:24][CH:23]=1>C(O)C>[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]2[NH:1][CH:2]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH:3]([C:4]3[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=3)[N:11]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 12282158HCID 12282158, compoundHCID 22996230HCID 22996230, compound

Product 1

HCID 178509632HCID 178509632, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[1,2-diamino-2-(4-chloro-phenyl)-ethyl]-benzonitrile (81 mg, 0.298 mmol) and ethyl 4-chloro-benzimidate hydrochloride (55 mg, 0.249 mmol) in ethanol (5 mL) was heated at 72° C. for 5 h. The solvent was removed, and the residue was taken in methylene chloride (10 mL). The reaction mixture was washed with 1 N sodium hydroxide solution (1 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0.5% methanol in methylene chloride yielded 4-[2,5-bis-(4-chloro-phenyl)-4,5-dihydro-3H-imidazol-4-yl]-benzonitrile (62 mg, 76%). HR-MS (EI, m/z) calculated for C22H15N3Cl2 (M+) 391.0643, observed 391.0648.

Workup

  1. customThe solvent was removed
  2. washThe reaction mixture was washed with 1 N sodium hydroxide solution (1 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solid was then filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  7. washeluting with 0.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-4d38753553434047ae9b7dd517e28c55
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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