Water → HCID 84657183, compound

HRID 524348Notes

Reaction equation

HRID 524348 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>O1CCCC1>[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 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-cyclopropylsulfanyl-benzamide (preparation 31a, 137 mg, 0.71 mmol) in dry tetrahydrofuran (1.0 mL) is added at 0° C. to a solution of lithium aluminium hydride in tetrahydrofuran (1 M, 2.1 mL, 2.1 mmol). The mixture is stirred at 0° C. for 1 h and heated at reflux for 1 h. The mixture is cooled at 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; Retention time HPLC: 0.51 min (X011_S03).

Workup

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

Sources & evidence

ORD record
ord-c70b79b8e0c94375b8c6197ef7c4b4c0
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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