Sodium Hydroxide → 4-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole

HRID 433583Notes

Reaction equation

HRID 433583 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([N:13]2[CH:17]=[C:16]([CH2:18]O)[N:15]=[CH:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12].[OH-].[Na+]>>[Cl:3][CH2:18][C:16]1[N:15]=[CH:14][N:13]([C:8]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([Cl:5])[CH:7]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 23444980HCID 23444980, compound

Product 1

HCID 234450324-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazoleYield 95%

Procedure

In an ice-bath thionyl chloride (39.5 ml, excess) was slowly added to [1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-methanol (9.6 g, 39.5 mmol). The resulting mixture was stirred for 24 h. After evaporation, the oily residue was triturated with ether and 10.12 g (86%) of the hydrochloride salt of the title compound was obtained as an off-white solid. To obtain the free base, the salt was carefully neutralized with aqueous NaOH (2N) and extracted with AcOEt. The organic phase was dried (Na2SO4) and concentrated to obtain 8.43 g (95%) of the title compound as an off-white solid. Mp. 146-147° C. dec. (AcOEt/hexane), MS: m/e=260 (M+)

Workup

  1. customAfter evaporation
  2. customthe oily residue was triturated with ether and 10.12 g (86%) of the hydrochloride salt of the title compound
  3. customwas obtained as an off-white solid
  4. customTo obtain the free base
  5. extractionextracted with AcOEt
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e77a5f18956b4e01b9b3a6e7a451dc17
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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