Tetrahydrofuran → HCID 14676633, compound

HRID 1164974Notes

Reaction equation

HRID 1164974 reaction equation
O1CCCC1.[CH2:6]([N:8]([CH2:24][CH3:25])[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=1)=O)[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C.O>[CH2:24]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=1)[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14676632HCID 14676632, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14676633HCID 14676633, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To tetrahydrofuran (15 mL) under a nitrogen atmosphere add 2.0 g (6.8 mmol) of 2-diethylamino-N-[4-[(methylsulfonyl)amino]phenyl]acetamide and 0.60 g (16 mmol) of lithium aluminum hydride. When the addition is complete stir the reaction at reflux. Monitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1). Upon completion of the reaction add 1 mL of H2O, 1 mL of 2N NaOH, 2 mL of water, and 50 mL ethyl acetate. The solid material is removed by suction filtration through celite and the solvent is removed in vacuo. Chromatrograph the resulting oil on silica gel with CH2Cl2 :MeOH, 9:1 followed by CH2Cl2MeOH, 2:1. Combine the product fractions and remove the solvent in vacuo. Dissolve the residue in 48% aqueous HBr and remove the solvent. Recrystallize from methanol/isopropanol to afford the title compound.

Workup

  1. additionWhen the addition
  2. customthe reaction
  3. temperatureat reflux
  4. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1)
  5. customThe solid material is removed by suction filtration through celite
  6. customthe solvent is removed in vacuo
  7. customCombine the product fractions and remove the solvent in vacuo
  8. dissolutionDissolve the residue in 48% aqueous HBr
  9. customremove the solvent
  10. customRecrystallize from methanol/isopropanol

Sources & evidence

ORD record
ord-e808e15a627d4d08b126ba6025c0d702
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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