Stannous Chloride → HCID 67980315, compound

HRID 406969Notes

Reaction equation

HRID 406969 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=2)=[C:4]([N+:23]([O-])=O)[CH:3]=1.[Sn](Cl)Cl>C(O)C>[NH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[C:4]([NH2:23])=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68054129HCID 68054129, compound

Product 1

HCID 67980315HCID 67980315, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl {3-[(4-bromo-2-nitrophenyl)amino]phenyl}carbamate (10.1 g, 24.7 mmol) and tin dichloride (24 g, 120 mmol, Aldrich, Cat. No. 208256) in ethanol (100 mL) was heated at 100° C. overnight. The solution was quenched with 1N NaOH aqueous solution, and then extracted with ethyl acetate twice. The combined organic phases were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to afford the desired compound (6.8 g, 99%). LCMS (M+H)+: m/z=278.0.

Workup

  1. customThe solution was quenched with 1N NaOH aqueous solution
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-80219ea881e24e2da397b73ff26c8af2
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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