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Ethylene Glycol → HCID 68598208, compound

HRID 1799675
Notes
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Reaction equation

HRID 1799675 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].[CH2:32]([OH:35])[CH2:33][OH:34]>C1COCC1.[Cl-].[Na+].O>[OH:34][CH2:33][CH2:32][O:35][CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 68601237HCID 68601237, compound

Product 1

HCID 68598208HCID 68598208, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; water
Solvent

Conditions

Temperature
50 °C

Procedure

4-Chloromethyl-5-((Z)-2-tritylthioethen-1-yl)thiazole (5.57 g) was suspended in 100 ml of THF and 30 ml of ethylene glycol, 1.5 g of sodium hydride was added to the suspension, and the mixture was stirred at 50° C. for 37 hr. Brine was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed twice with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) to give 4.87 g of the title compound.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwere washed twice with brine
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationwere filtered
  5. concentrationwere concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-d119cf5852e44a368a23ab8db42d7e5c
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08344154B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes