Water → HCID 57687714, compound

HRID 2194667Notes

Reaction equation

HRID 2194667 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., 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. Tetrahydrofuran was added to the obtained gel and the mixture was filtered. The filtrate was concentrated under reduced pressure. A mixed solution of ethyl acetate-diisopropyl ether (1:1) was added to the residue, and insoluble crystals were collected by filtration to give the title compound as pale-yellow crystals (yield 797 mg, yield 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 solution of ethyl acetate-diisopropyl ether (1:1) was added to the residue, and insoluble crystals
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ee18a99eca3246ac9f536b377d4ce7fd
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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