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Acetic Anhydride → (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)-2-propenoic acid

HRID 36977
Notes
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Reaction equation

HRID 36977 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26]([OH:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)(=O)C>O>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7](/[CH:10]=[C:25](/[C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)\[C:26]([OH:28])=[O:27])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 159702-Thiopheneacetic acidHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-

Product 1

HCID 69948967(E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (2 mmol), 2-thienylacetic acid (2.3 mmol), potassium carbonate (0.91 mmol), and acetic anhydride (1 mL) is heated gradually to 140° C. and held at this temperature for 6 hours. The cooled reaction is diluted with water and the solid is separated, triturated several times with ether, and the solid is crystallized to give the title compound.

Workup

  1. customThe cooled reaction
  2. customthe solid is separated
  3. customtriturated several times with ether
  4. customthe solid is crystallized

Sources & evidence

ORD record
ord-9f5c38a8d3ec4df8a69471349893b3ad
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05418250

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes