Benzylamine → HCID 19774261, compound

HRID 1029745Notes

Reaction equation

HRID 1029745 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]CS([O-])(=O)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:19]([NH:26][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 19774265HCID 19774265, compound

Product 1

HCID 19774261HCID 19774261, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methanesulfonamidophenyl)ethylmethanesulfonate (XXXII) (20 g), benzylamine (7.0 g) and triethylamine (15 ml) were combined in dimethylformamide (75 ml) and heated 18 hours at 100°. The solvent was evaporated and the residue was dissolved in EtOAc, which was washed with saturated NaHCO3, dried (MgSO4) and evaporated to give a dark oil. This was chromatographed on a silica column, eluting 8.0 g of solid product with CHCl3 /MeOH/concentrated NH4OH (15:1:0.1). This solid was treated with MeOH/concentrated HCl (10:1), causing precipitation of 4'-(2-benzylaminoethyl)methanesulfonanilide.HCl (XXIX.HCl), m.p. 244°-245°, whose NMR was consistent with the proposed structure.

Workup

  1. temperatureheated 18 hours at 100°
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwhich was washed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a dark oil
  8. customThis was chromatographed on a silica column
  9. washeluting 8.0 g of solid product with CHCl3 /MeOH/concentrated NH4OH (15:1:0.1)
  10. additionThis solid was treated with MeOH/concentrated HCl (10:1)
  11. customprecipitation of 4'-(2-benzylaminoethyl)methanesulfonanilide

Sources & evidence

ORD record
ord-2eda7e580322408ab4d4c4281a8e6539
Source dataset
uspto-grants-1992_04
Patent number
US05102914

Reaction notes

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