Hydrochloric Acid → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-

HRID 1857761Notes

Reaction equation

HRID 1857761 reaction equation
Cl.C([O:9][CH2:10][CH2:11][C:12]1[N:13]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:27][C:25]1[CH:26]=[C:21]([S:20][C:14]2[N:13]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)[C:12]([CH2:11][CH2:10][OH:9])=[N:16][C:15]=2[CH:17]([CH3:19])[CH3:18])[CH:22]=[C:23]([Cl:28])[CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178907742-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole

Product 1

HCID 4740671H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-Yield 33%

Procedure

To 5 ml of concentrated hydrochloric acid was dissolved 1.3 g (2.34 mmol) of the benzyl compound (125a), the mixture was refluxed with heating for 4 hours and worked up. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and dried, distilled off, the residual oil was treated with ether, arid crystallized to give 5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole (126a). m.p. 169-171° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationdistilled off
  7. additionthe residual oil was treated with ether, arid
  8. customcrystallized

Sources & evidence

ORD record
ord-6a4ca3a180004b94ae23b9a5f3512706
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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