Ammonium Chloride → [8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol

HRID 1399298Notes

Reaction equation

HRID 1399298 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23](OC)=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=3[Cl:22])[CH2:12][CH2:13][N:7]21.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=4[Cl:22])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH2:23][OH:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 57785906Methyl 8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate

Product 1

HCID 57785983[8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (200 mg, 0.487 mmol) in tetrahydrofuran (10 mL) was added lithium tetrahydroborate (53 mg, 2.43 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 days. Aqueous ammonium chloride was added to the reaction mixture at 0° C. and the mixture was concentrated in vacuo. The precipitated solid was collected by filtration, washed with water, 2-propanol and diisopropyl ether to give the title compound (165.9 mg, 0.43 mmol, 89%) as a colorless solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water, 2-propanol and diisopropyl ether

Sources & evidence

ORD record
ord-c45addf22d29476982053de763dd0c7a
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…