Hydrogen chloride-ethyl acetate → 2-(5-chloro-2-oxo-1,3-benzoxazol-3 (2H)-yl)-N-{[5,6-dichloro-1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamide hydrochloride

HRID 1428411Notes

Reaction equation

HRID 1428411 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH2:16][C:17]3[N:21]([CH2:22][CH2:23][O:24]COC)[C:20]4[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:19]=4[N:18]=3)[CH3:15])=[O:13])[C:6]=2[CH:34]=1.Cl.CCOC(C)=O>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH2:16][C:17]3[N:21]([CH2:22][CH2:23][OH:24])[C:20]4[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:19]=4[N:18]=3)[CH3:15])=[O:13])[C:6]=2[CH:34]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 1176525882-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-({5,6-dichloro-1-[2-(methoxymethoxy)ethyl]-1H-benzimidazol-2-yl}methyl)-N-methylacetamide

Product 1

HCID 1176524992-(5-chloro-2-oxo-1,3-benzoxazol-3 (2H)-yl)-N-{[5,6-dichloro-1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamide hydrochlorideYield 156.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-({5,6-dichloro-1-[2-(methoxymethoxy)ethyl]-1H-benzimidazol-2-yl}methyl)-N-methylacetamide (110 mg) and MeOH (0.22 mL) was added 4 M hydrogen chloride/EtOAc (521 μL), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The obtained solid was washed with EtOAc to obtain 2-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-{[5,6-dichloro-1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamide hydrochloride (85 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washThe obtained solid was washed with EtOAc

Sources & evidence

ORD record
ord-a3cf4a0c9fb04796abb4aa3ea6f6f8b1
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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