Stannous Chloride → Ethyl 3-(3-aminophenyl)-3-benzenesulphonylamino-propionate

HRID 1596560Notes

Reaction equation

HRID 1596560 reaction equation
[Sn](Cl)Cl.[C:4]1([S:10]([NH:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=2)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C(O)C>[NH2:27][C:23]1[CH:22]=[C:21]([CH:14]([NH:13][S:10]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:12])=[O:11])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 11188106Ethyl 3-benzenesulphonylamino3-(3-nitrophenyl)-propionate

Product 1

HCID 15907252Ethyl 3-(3-aminophenyl)-3-benzenesulphonylamino-propionateYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.77 g of tin-(II) chloride were added to a solution of 2.0 g of (1c) in 60 ml of ethanol, and the reaction mixture was heated under reflux for 2 h. After cooling, the solution was hydrolysed by pouring it onto ice and adjusted to pH=8 using an NaHCO3 solution (5%). It was then extracted with dichloromethane and the organic phase was washed with NaCl, dried over MgSO4 and concentrated. 1.79 g of a yellow oil were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. additionby pouring it onto ice
  5. extractionIt was then extracted with dichloromethane
  6. washthe organic phase was washed with NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-37abd91027c74af68b4bc6e201734692
Source dataset
uspto-grants-2001_09
Patent number
US06291503B1

Reaction notes

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