Stannous chloride dihydrate → 3-amino-4-[(3-furylmethyl)amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 2217941Notes

Reaction equation

HRID 2217941 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][C:8]2[CH:26]=[CH:25][C:11]([C:12]([N:14]([CH2:20][C:21]([F:24])([F:23])[F:22])[CH2:15][C:16]([F:19])([F:18])[F:17])=[O:13])=[CH:10][C:9]=2[N+:27]([O-])=O)=[CH:2]1.O.O.[Sn](Cl)Cl>CN(C=O)C>[NH2:27][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][C:8]=1[NH:7][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[C:12]([N:14]([CH2:20][C:21]([F:22])([F:23])[F:24])[CH2:15][C:16]([F:18])([F:19])[F:17])=[O:13]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 588744814-[(3-Furylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 588744893-amino-4-[(3-furylmethyl)amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(3-Furylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (108 mg, 0.254 mmol) was dissolved in 5 mL of DMF. Tin(II) chloride dihydrate (860 mg, 1.27 mmol) was added and the solution was stirred under nitrogen at RT for 24 h. The solvent was evaporated and the residue was taken up in EtOAc. The organic phase was washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was used directly for the next step. Yield: 80 mg (80%); MS (ESI) 396.11 (MH+).

Workup

  1. customThe solvent was evaporated
  2. washThe organic phase was washed with saturated NaHCO3 solution, brine
  3. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-2977551e6d3c4af9b9a07d5471343eb6
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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