Stannous chloride dihydrate → 3-Amino-4-methyl-N-(3-(2-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 1465014Notes

Reaction equation

HRID 1465014 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[CH3:24])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:27]([O-])=O.O.O.Cl[Sn]Cl>C(O)C.C(OCC)(=O)C>[NH2:27][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:2]=1[CH3:1])[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[CH3:24])[CH:10]=1)=[O:7]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 682633374-Methyl-N-(3-(2-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)phenyl)-3-nitrobenzamide

Product 1

HCID 673766623-Amino-4-methyl-N-(3-(2-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The compound (27 g, 72.1 mmol) obtained in Step 2 of Preparation Example 6 was dissolved in ethanol (300 mL), SnCl2.2H2O (81 g, 360 mmol) was added thereto and stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 solution several times. The organic layer was dried with anhydrous MgSO4, filtered and concentrated to obtain the title compound without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with sat. NaHCO3 solution several times
  3. dry with materialThe organic layer was dried with anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bc04bc5b937436daf0d9b4b47cc1e5b
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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