Anisole → HCID 86585652, compound

HRID 1167994Notes

Reaction equation

HRID 1167994 reaction equation
[C:1]1([O:7]C)C=CC=C[CH:2]=1.[CH:9]1[C:22]2[C:13](=[N:14][C:15]3[C:20]([C:21]=2[NH:23][C:24]2[CH:25]=[C:26]([CH:39]=[C:40]([CH2:42][OH:43])[CH:41]=2)[NH:27]C(=O)CNC(=O)OC(C)(C)C)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(#[N:50])C.ClCCl>>[CH:19]1[C:20]2[C:15](=[N:14][C:13]3[C:22]([C:21]=2[NH:23][C:24]2[CH:25]=[C:26]([NH:27][NH:50][C:1](=[O:7])[CH3:2])[CH:39]=[C:40]([CH2:42][OH:43])[CH:41]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 21877088Acetonitrile methylene chlorideHCID 22994848HCID 22994848, compound

Product 1

HCID 86585652HCID 86585652, compoundYield 62.7%

Procedure

Anisole (0.47 g, 4.28 mmol) and acetonitrile/dichloromethane (1/2, v/v, 25 ml) were added to t-butyl N-{2-[3-(9-acridinylamino)-5-(hydroxymethyl)anilino]-2-oxoethyl}carbamate (0.34 g, 0.71 mmol). To the resulting mixture, aluminium chloride (0.57 g, 4.28 mmol) was slowly added with stirring and stirred for 2 hours at the room temperature. The resulting product was concentrated under the reduced pressure and purified by column chromatography to give the titled compound.

Workup

  1. stirringstirred for 2 hours at the room temperature
  2. concentrationThe resulting product was concentrated under the reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-fbbcc5cc977641479e84f52202bedfca
Source dataset
uspto-grants-2003_09
Patent number
US06620936B2

Reaction notes

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