Potassium thiocyanate → HCID 178497764, compound

HRID 491841Notes

Reaction equation

HRID 491841 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([NH:11][CH2:12][C:13]([C:15]2[CH:16]=[N:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:19]=2[CH3:20])=O)[CH:5]=1.[C:28]([S-:30])#[N:29].[K+]>CC(O)=O>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH:12]=[C:13]([C:15]3[CH:16]=[N:17][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:19]=3[CH3:20])[N:29]=[C:28]2[SH:30])[CH:5]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 588612934-methyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-benzoic acid methyl ester

Product 1

HCID 178497764HCID 178497764, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 380 mg (1.05 mmol) of 4-methyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-benzoic acid methyl ester and 203 mg (2.09 mmol) of KSCN in 4 mL of HOAc was stirred at 100° C. for 4 h, when a precipitate formed. The mixture was cooled to room temperature, filtered, and washed with cold MeOH to provide 283 mg of 3-[2-mercapto-4-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzoic acid methyl ester (0.70 mmol, 67%). ESI MS m/z 405 [C22H20N4O2S+H]+.

Workup

  1. customwhen a precipitate formed
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washwashed with cold MeOH

Sources & evidence

ORD record
ord-2439bb47448c4e059a42085d9874919c
Source dataset
uspto-grants-2009_05
Patent number
US07531560B2

Reaction notes

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