HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 1H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-(2-hydroxyethyl)-4-(1-methylethyl)-

HRID 1857781
Notes
Print preview

Reaction equation

HRID 1857781 reaction equation
Cl.C([O:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]([CH2:30][CH2:31][OH:32])[C:15]([S:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:29][C:24]1[CH:23]=[C:22]([S:21][C:15]2[N:14]([CH2:30][CH2:31][OH:32])[C:13]([CH2:12][CH2:11][CH2:10][OH:9])=[N:17][C:16]=2[CH:18]([CH3:20])[CH3:19])[CH:27]=[C:26]([Cl:28])[CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4741011H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(3-(phenylmethoxy)propyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 4741021H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-(2-hydroxyethyl)-4-(1-methylethyl)-Yield 26.6%

Conditions

Temperature
110 °C

Procedure

To 14 ml of concentrated hydrochloric acid, 1.4 g (2.9 mmol) of the alcohol (136e) was added and the mixture was heated at 110° C. For 7 hours. After cooling, the mixture was neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol-ethyl acetate) to provide 300 mg (yield 26%) of 3-(5-(3,5-dichlorophenylthio)-1-(2-hydroxyethyl)-4-isopropyl-1H-imidazol-2-yl)-propan-1-ol (137d) as oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-55af980e02794eb59d6d4d8c004f417d
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes