Lithium Chloride → [1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

HRID 714629Notes

Reaction equation

HRID 714629 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[C:13](OCC)=[O:14].[Cl-].[Li+].[BH4-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>COCCOC>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 9855836Potassium sodium tartarateHCID 67409298Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate

Product 1

HCID 67410386[1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1200 mg (3.5 mmol) of the compound from Example 33A together with 15 mg (0.35 mmol) of lithium chloride were dissolved in 53 ml 1,2-dimethoxyethane, and 198 mg (5.23 mmol) of sodium borohydride were added at 0° C. The mixture was stirred at RT for 1 h. For work-up, 25 ml of a saturated potassium sodium tartrate solution were added with ice cooling and the mixture was extracted with 50 ml of ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1). This gave 800 mg (76% of theory) of the target compound.

Workup

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-dd5f10d1e3d04799aab6c5d482bccdb3
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…