Water → HCID 57687714, compound

HRID 1670874Notes

Reaction equation

HRID 1670874 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([C:12](OCC)=[O:13])[N:9]=[C:8]2[S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[C:8]2[S:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 57687715HCID 57687715, compound

Product 1

HCID 57687714HCID 57687714, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution (30 mL) of ethyl 1-phenyl-2-(phenylthio)-1H-imidazole-4-carboxylate (1.17 g) in tetrahydrofuran was cooled to −70° C., and a 1.5 mol/L solution (12 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The reaction mixture was stirred at 0° C. for 4 hr, water was added, and the mixture was stirred for 30 min. To the obtained gel-like substance was added tetrahydrofuran, the mixture was filtered, and the filtrate was concentrated under reduced pressure. A mixed solvent of ethyl acetate-diisopropyl ether (1:1) was added to the residue and the resulting unsoluble crystals were collected by filtration to give the title compound as pale-yellow crystals (yield 797 mg, 78%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionA mixed solvent of ethyl acetate-diisopropyl ether (1:1) was added to the residue
  5. filtrationthe resulting unsoluble crystals were collected by filtration

Sources & evidence

ORD record
ord-0af581ce10364aea873e7e6dbdf05d9f
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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