Water → HCID 7131744, compound

HRID 2041167Notes

Reaction equation

HRID 2041167 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.O>C1COCC1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 7163534-(2-methyl-1,3-thiazol-4-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 7131744HCID 7131744, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 4-(2-methylthiazol-4-yl)-benzonitrile (305 mg, 1.52 mmol) in anhydrous THF (50 mL). Add a 1M solution of lithium aluminum hydride in THF (3.05 mL, 3.05 mmol). Heat the mixture overnight under reflux. Cool the reaction mixture with ice/water and work-up sequentially with EtOAc and water. Filter the mixture over Celite®. Separate the organic phase, and extract the aqueous phase with chloroform. Dry the combined organic extracts over Na2SO4, filter and concentrate to obtain the title compound as an oil (120 mg) that was used without further purification. GC-MS m/z: 204 (M+).

Workup

  1. temperatureHeat the mixture overnight
  2. temperatureunder reflux
  3. filtrationFilter the mixture over Celite®
  4. customSeparate the organic phase
  5. extractionextract the aqueous phase with chloroform
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-5e2947e79ad14b72bb3b7fb679ddce25
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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