Aluminium lithium hydride → HCID 67043922, compound

HRID 1944457Notes

Reaction equation

HRID 1944457 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[S:10](=[O:20])(=[O:19])[N:11]([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.O>[CH3:18][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[S:10]([C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67044583HCID 67044583, compound

Product 1

HCID 67043922HCID 67043922, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A mixture of 2-(methylphenylsulfamoyl)nicotinic acid methyl ester (1.5 g) and tetrahydrofuran (50 mL) at −78° C. was treated with a 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (10 mL), and the resulting mixture was stirred at −78° C. for 1 hour and then at room temperature for 2 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined organic extract was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (1:0 to 19:1 by volume) to afford the title compound (0.25 g).

Workup

  1. waitat room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. extractionthe combined organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and methanol (1:0 to 19:1 by volume)

Sources & evidence

ORD record
ord-e8655701d70448c8978d804f0da85913
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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