Water → HCID 84657183, compound

HRID 527367Notes

Reaction equation

HRID 527367 reaction equation
[CH:1]1([S:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=O)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH:1]1([S:4][C:5]2[CH:13]=[CH:12][C:8]([CH2:9][NH2:11])=[CH:7][CH:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86711600HCID 86711600, compound

Product 1

HCID 84657183HCID 84657183, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-cyclopropylsulfanyl-benzamide (preparation 63a, 137 mg, 0.71 mmol) in THF is added to lithium aluminium hydride (1 M in THF, 2.1 mL, 2.1 mmol) precooled at 0° C. The mixture is stirred at 0° C. for 1 h and then heated at reflux for 1 h. The mixture is cooled to room temperature and stirred for 1.5 h. Water is added, and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. Yield: 75 mg (60% of theory); ESI mass spectrum: [M+H]+=180; r.t. HPLC: 0.51 min (X011_S03).

Workup

  1. customprecooled at 0° C
  2. temperatureheated
  3. temperatureat reflux for 1 h
  4. temperatureThe mixture is cooled to room temperature
  5. stirringstirred for 1.5 h
  6. extractionthe mixture is extracted twice with dichloromethane
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customr.t
  10. custom0.51 min (X011_S03)

Sources & evidence

ORD record
ord-92a5df36727f4b6cbc1182e4aff77c0e
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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