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Ethyl Acetate → HCID 178418534, compound

HRID 3781
Notes
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Reaction equation

HRID 3781 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].BrC[C:23]1[S:24][C:25]([O:28][CH2:29][CH3:30])=[N:26][N:27]=1.C(OCC)(=O)C>CC(C)=O>[CH2:29]([O:28][C:25]1[SH:24]([CH3:15])[C:23]([O:14][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)=[N:27][N:26]=1)[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 201533922-Bromomethyl-5-ethoxy-1,3,4-thiadiazole

Product 1

HCID 178418534HCID 178418534, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

0.76 g of 4-phenoxy phenol was dissolved in 10 ml of acetone followed by adding 0.6 g of anhydrous potassium carbonate and 1.0 g of 2-bromomethyl-5-ethoxy-1,3,4-thiadiazole. The resulting mixture was refluxed with stirring and heated for 2 hours. After cooling, 100 ml of ethyl acetate was added followed by washing with water for two times, and the resulting ethyl acetate layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled over under reduced pressure, and the residue was purified by chromatography on silica gel to obtain 1.0 g of the compound No. 1 described in Table 1.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureheated for 2 hours
  3. temperatureAfter cooling
  4. washby washing with water for two times
  5. dry with materialthe resulting ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled over under reduced pressure
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f72db97d8ce54dbba8cafdb5ed72d91d
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04722934

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes