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Ethyl bromoacetate → HCID 474100, compound

HRID 1857779
Notes
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Reaction equation

HRID 1857779 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:13][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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>C(#N)C>[C:37]([O:39][CH2:40][CH2:41][N:13]1[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]=[C:12]1[CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:38])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178440070HCID 178440070, compound

Product 1

HCID 474100HCID 474100, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In 50 ml of dry acetonitrile was dissolved 5.0 g (11.5 mmol) of the imidazole (101e), followed by addition of 3.2 g (23.2 mmol) of potassium carbonate and 2.9 g (17.4 mmol) of ethyl bromoacetate, and the mixture was heated at 60° C. for 11 hours. The reaction mixture was diluted with ice-water 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 (ethyl acetate:n-hexane=1:2) to provide 5.75 g (yield 96%) of (2-(3-benzyloxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)-ethyl acetate (136d) as oil.

Workup

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

Sources & evidence

ORD record
ord-0418743080f34ce29497b83f7d20a6c4
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes