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Water → ethyl 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylate

HRID 1717337
Notes
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Reaction equation

HRID 1717337 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]=[N:13]2)=[C:8]([OH:22])[CH:7]=1)=[O:5])[CH3:2].Br[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]=[N:13]2)=[C:8]([O:22][CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:7]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 68517012ethyl 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 68515694ethyl 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylateYield 57%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxylate (0.30 g) obtained in Example 133c) in DMF (10 ml) were added (3-bromopropyl)benzene (0.18 ml) and potassium carbonate (0.14 g), and the mixture was stirred overnight at 75° C. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) and recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow powder (0.25 g, 57%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c86258cc69ff4fc7ab8384a97ce3a31d
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes