Ammonia → HCID 69274217, compound

HRID 749301Notes

Reaction equation

HRID 749301 reaction equation
[F:1][C@H:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][NH:4]S(C1C=CC(C)=CC=1)(=O)=O.N.[Na]>CO>[F:1][C@H:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 69274294HCID 69274294, compound

Product 1

HCID 69274217HCID 69274217, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a two necked flask equipped with a dry ice condenser was added (R)-N-(2-Fluoro-3-phenylpropyl)-4-methylbenzenesulfonamide (1.0 g) and ammonia gas to condense about 25 mL of liquid. Small pieces of sodium were added to the stirred solution until a dark orange color persisted for 5 min. Methanol was added to quench the reaction. After evaporation of the ammonia the product was dissolved in MeOH, filtered, and concentrated. The residue was extracted into chloroform and chromatographed over silica gel with an ammoniated mixture of MeOH/ether (1:19) to give 0.14 g of the title compound as an oil. MS ES (M++H-NH3)=136.

Workup

  1. customTo a two necked flask equipped with a dry ice condenser
  2. customto quench
  3. customthe reaction
  4. customAfter evaporation of the ammonia the product
  5. dissolutionwas dissolved in MeOH
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionThe residue was extracted into chloroform
  9. customchromatographed over silica gel with an ammoniated mixture of MeOH/ether (1:19)

Sources & evidence

ORD record
ord-b82cd00001ae4640a1ecd1847bde3d58
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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