Potassium Carbonate → ethyl 2-[2-(4-cyanophenyl)-2-oxo-ethylthio]-3H-imidazole-4-carboxylate

HRID 844256Notes

Reaction equation

HRID 844256 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([SH:11])[NH:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25]Br)=[CH:22][CH:21]=1)#[N:19]>C(#N)C>[C:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25][S:11][C:8]2[NH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:10][N:9]=2)=[CH:22][CH:21]=1)#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 986544-(Bromoacetyl)benzonitrileHCID 178469909HCID 178469909, compound

Product 1

HCID 22612522ethyl 2-[2-(4-cyanophenyl)-2-oxo-ethylthio]-3H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 4-ethoxycarbonylimidazole-2-thiol (8.22 g, 47.8 mmol) and potassium carbonate (19.8 g, 143 mmol) in dry acetonitrile (100 mL) at room temperature was added 4-cyanophenacyl bromide (10.7 g, 47.8 mmol). The reaction mixture was stirred for 20 hours, during which time a white precipitate formed. To the solution was added 100 mL ice water. The resulting solid was filtered and washed with water (2×25 mL) to provide the title product as an off-white solid which was sufficiently pure for use in the next step.

Workup

  1. customformed
  2. filtrationThe resulting solid was filtered
  3. washwashed with water (2×25 mL)

Sources & evidence

ORD record
ord-fa53b49c49524e9b860fa48aac6023d1
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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