HCID 17446227, compound → HCID 59828858, compound

HRID 1190949Notes

Reaction equation

HRID 1190949 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[N:13]=1>C1COCC1>[CH3:7][NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=2)[N:13]=1

Participants

4

Reactant 2

HCID 17446227HCID 17446227, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59828858HCID 59828858, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1M lithium aluminum hydride in THF (5.6 mL, 5.6 mmol) under nitrogen to a solution of 4-(2-methylamino-thiazol-4-yl)-benzonitrile (0.4 g, 1.86 mmol) in anhydrous THF (5 mL). After gas evolution stops, heat the reaction mixture to reflux for 30 min. Cool to room temperature, quench by slow addition of water (0.5 mL), 5N aqueous NaOH (5 mL) and additional water (1.5 mL). Add EtOAc (50 mL), stir vigorously for 20 min and filter through Celite®. Separate and dry the organic phase over Na2SO4. Concentrate in vacuo to obtain the title compound (0.4 g, 98%) as a white solid suitable for use without additional purification. MS (ES+) m/z: 220 (M+H)+.

Workup

  1. temperatureheat the reaction mixture
  2. temperatureto reflux for 30 min
  3. customquench by slow addition of water (0.5 mL), 5N aqueous NaOH (5 mL) and additional water (1.5 mL)
  4. filtrationfilter through Celite®
  5. customSeparate
  6. dry with materialdry the organic phase over Na2SO4
  7. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-751de052e15441aa863664c225e08e48
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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