Tetrahydrofuran → HCID 23445108, compound

HRID 433582Notes

Reaction equation

HRID 433582 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:10]=1[CH3:11])=O)C.C1COCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>>[Cl:19][C:14]1[CH:13]=[C:12]([N:9]2[C:10]([CH3:11])=[C:6]([CH2:4][OH:3])[N:7]=[CH:8]2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 690427491-(3,4-dichloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 23445108HCID 23445108, compound

Procedure

To a solution of 1-(3,4-dichloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester (0.82 g, 2.7 mmol) in THF (27 ml) lithium aluminum hydride (0.21 g, 5.4 mmol) was added portionwise keeping T<10° C. The mixture was stirred in an ice-bath for 2 h, then 1 ml saturated aqueous Seignette salt solution was slowly added. After dilution with AcOEt (100 ml) the mixture was filtered, concentrated and chromatographed [silica, elution with gradient CH2Cl2 to 80% (CH2Cl2/MeOH=9:1)]. The title compound was obtained as a white crystalline solid (0.46 g, 66%). Mp. 174-175° C. (CH2Cl2/iPr2O), MS: m/e=256 (M+)

Workup

  1. filtrationAfter dilution with AcOEt (100 ml) the mixture was filtered
  2. concentrationconcentrated
  3. customchromatographed
  4. wash[silica, elution with gradient CH2Cl2 to 80% (CH2Cl2/MeOH=9:1)]

Sources & evidence

ORD record
ord-fd0c8ce8b9a9463b864185e0e396d96d
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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