Water → HCID 178497763, compound

HRID 491846Notes

Reaction equation

HRID 491846 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([NH:11][CH2:12][C:13](=O)[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=1.[C:22]([S-:24])#[N:23].[K+].O.[OH-].[Na+]>CC(O)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH:12]=[C:13]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:23]=[C:22]2[SH:24])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516872Potassium thiocyanateHCID 58861443HCID 58861443, compound

Product 1

HCID 178497763HCID 178497763, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methyl-3-(2-oxo-2-pyridin-3-yl-ethylamino)-benzoic acid methyl ester (84.5 mg, 0.297 mmol) and KSCN (58 mg; 0.59 mmol) in 1.5 mL of HOAc were heated to 100° C. for 2 h. The mixture was then poured into water and carefully brought to pH 8 with NaOH. The mixture was immediately extracted with EtOAc, and the extract washed with brine. The washes were extracted once more with EtOAc, and the combined extracts were dried with Na2SO4, filtered, and concentrated to provide 3-(2-mercapto-4-pyridin-3-yl-imidazol-1-yl)-4-methyl-benzoic acid methyl ester (90 mg, 0.28 mmol; 93%). ESI MS m/z 326 [C17H15N3O2S+H]+.

Workup

  1. extractionThe mixture was immediately extracted with EtOAc
  2. washthe extract washed with brine
  3. extractionThe washes were extracted once more with EtOAc
  4. dry with materialthe combined extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd91c3cd0f7c4a4a8520d0d9a32b323b
Source dataset
uspto-grants-2009_05
Patent number
US07531560B2

Reaction notes

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