Ammonium Chloride → HCID 22731423, compound

HRID 1356718Notes

Reaction equation

HRID 1356718 reaction equation
[C:1]([C:5]1[O:9][C:8]([C:10](O)=[O:11])=[CH:7][C:6]=1[S:13](=[O:16])(=[O:15])[NH2:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1.CCCCCC>[C:1]([C:5]1[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=1[S:13]([NH2:14])(=[O:16])=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22731415HCID 22731415, compound

Product 1

HCID 22731423HCID 22731423, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Under cooling with ice, a solution of methyl ester of 5-tert-butyl-4-sulfamoyl-furan-2-carboxylic acid (1.90 g) in THF (20 ml) was added dropwise to a suspension of lithium aluminum hydride (0.55 g) in THF (10 ml) over 35 min., followed by stirring for 2 hours. The reaction mixture was diluted with n-hexane, mixed with saturated aqueous ammonium chloride (5 ml) and filtered on Celite, being washed with ethyl acetate. The filtrate was dried over magnesium sulfate and evaporated to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=1:1) to give the titled compound (1.66 g, 98%).

Workup

  1. temperatureUnder cooling with ice
  2. filtrationfiltered on Celite
  3. washbeing washed with ethyl acetate
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent

Sources & evidence

ORD record
ord-c74c0ba602f840069e31c81e1a6d94ae
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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