Potassium thiocyanate → HCID 178435404, compound

HRID 2109303Notes

Reaction equation

HRID 2109303 reaction equation
[CH3:1][O:2][C:3](=[O:28])[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:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]=2[CH2:20][CH3:21])=O)[CH:5]=1.[C:29]([S-:31])#[N:30].[K+]>CC(O)=O>[CH3:1][O:2][C:3](=[O:28])[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:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19]=3[CH2:20][CH3:21])[N:30]=[C:29]2[SH:31])[CH:5]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 58861396HCID 58861396, compound

Product 1

HCID 178435404HCID 178435404, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3.75 g (9.94 mmol) of 3-[2-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-4-methyl-benzoic acid methyl ester and 2.9 g (30 mmol) of KSCN in 25 mL of HOAc was stirred at 100° C. for 4 h. The mixture was allowed to cool overnight before being filtered and washed with cold MeOH. The solids were dried to provide 2.65 g of 3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-2-mercapto-imidazol-1-yl]-4-methyl-benzoic acid methyl ester as an off-white solid. ESI MS m/z 419 [C23H22N4O2S+H]+.

Workup

  1. temperatureto cool overnight
  2. filtrationbefore being filtered
  3. washwashed with cold MeOH
  4. customThe solids were dried

Sources & evidence

ORD record
ord-427b03b62a9d4a38a5033562e1f17658
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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