Methyl p-toluenesulfonate → HCID 13881298, compound

HRID 231578Notes

Reaction equation

HRID 231578 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[S:13]([NH:16][CH2:17][CH2:18][OH:19])(=[O:15])=[O:14].[H-].[Na+].[Na].[C:25]1(C)C=CC(S(OC)(=O)=O)=CC=1>CN(C=O)C.C(Cl)CCC.CCOC(C)=O>[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[S:13]([N:16]([CH2:17][CH2:18][OH:19])[CH3:25])(=[O:15])=[O:14]

Participants

8

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 5360545SodiumHCID 13881297HCID 13881297, compound

Product 1

HCID 13881298HCID 13881298, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent3×HCID 8005Butyl ChlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N,N-Dimethyl-2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzamide (3.97 g, 12.5 mmol) in dry DMF (40 ml) was added slowly to a stirred suspension of 50% NaH (0.60 g, 12.5 mmol) in dry DMF (10 ml) under N2 at 20-25°. After formation of the sodium salt was complete, a solution of methyl p-toluenesulfonate (2.40 g, 12.9 mmol) in DMF (4 ml) was added and the reaction mixture stirred at 20-25° for 20 hours and then at 60° for 23 hours. The orange solution was mixed with EtOAc (400 ml) and the white solid which formed was filtered off. This precipitate was washed with EtOAc (100 ml). The combined EtOAc solutions were washed with a saturated aqueous NaCl solution, dried (Na2SO4), filtered and concentrated under reduced pressure. Pure produced, mp 107-08°, 2.5 g (60%) was obtained by flash chromatography over silica gel and elution with a 65% n-butylchloride-35% acetonitrile solvent mixture.

Workup

  1. waitat 60° for 23 hours
  2. customthe white solid which formed
  3. filtrationwas filtered off
  4. washThis precipitate was washed with EtOAc (100 ml)
  5. washThe combined EtOAc solutions were washed with a saturated aqueous NaCl solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPure produced

Sources & evidence

ORD record
ord-0c88ae8ceca3423ca47c4bce13a30d22
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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