HCID 59333282, compound → HCID 59333338, compound

HRID 1893488Notes

Reaction equation

HRID 1893488 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[C:12]([N+:20]([O-])=O)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[C:12]([NH2:20])=[CH:11][C:10]=1[C:23]([F:26])([F:24])[F:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 59333282HCID 59333282, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59333338HCID 59333338, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-benzyl-5-(1H-imidazol-1-yl)-4-nitro-2-(trifluoromethyl)aniline (190 mg; 0.52 mmol; 1 eq) and tin chloride dihydrate (591 mg; 2.62 mmol; 5 eq) in ethanol (2 ml) is stirred under argon at 80° C. for 4 h. Concentration, partition (ethyl acetate/aqueous sodium hydrogenocarbonate), addition of solid sodium hydrogenocarbonate to adjust the pH around 8, filtration over Celite, extraction of the cake solid with ethyl acetate, reunion of the organic phases, additional washings (aqueous ammonium chloride, brine), drying (magnesium sulfate) and concentration affords the title product (165 mg; 0.50 mmol; 96%) as a yellow solid.

Workup

  1. concentrationConcentration
  2. custompartition
  3. addition(ethyl acetate/aqueous sodium hydrogenocarbonate), addition of solid sodium hydrogenocarbonate
  4. filtrationthe pH around 8, filtration
  5. extractionover Celite, extraction of the cake solid with ethyl acetate, reunion of the organic phases, additional washings (aqueous ammonium chloride, brine)
  6. customdrying
  7. concentration(magnesium sulfate) and concentration

Sources & evidence

ORD record
ord-c2001724a2614fefa0682d2a474a7731
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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