Stannous chloride dihydrate → HCID 19605536, compound

HRID 1603623Notes

Reaction equation

HRID 1603623 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:20]([CH3:24])[C:21](=[O:23])[CH3:22])[CH:5]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:20]([CH3:24])[C:21](=[O:23])[CH3:22])[CH:5]=[C:6]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 19605537HCID 19605537, compound

Product 1

HCID 19605536HCID 19605536, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

0.04 g (0.00009 mol) of N-[3-bromo-5-(4-nitrobenzenesulphonyl) -phenyl]-N-methylacetamide was dissolved in 5 ml of ethanol, treated while cooling with a solution of 0.085 g (0.00045 mol) of SnCl2.2H2O in 0.34 ml of HCl (37%) and stirred at room temperature for 18 hrs. Then, the solvent was removed and the residue was adjusted to pH 8 with sat. NaHCO3 solution. The aqueous phase was extracted with ethyl acetate and the organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and freed from solvent. There was obtained 0.021 g (61%) of N-[3-bromo-5-(4-aminobenzenesulphonyl)-phenyl]-N-methylacetamide as a light yellow oil. MS (ISN): me/e=443, 441 (C15H15BrN2O3S- +NaOAc).

Workup

  1. additiontreated
  2. customThen, the solvent was removed
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe organic phase was washed with sat. sodium chloride solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2b3a1638a7a2495c9ddb15a2f4c6e8aa
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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