Tin tetrachloride → HCID 68940820, compound

HRID 2218682Notes

Reaction equation

HRID 2218682 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH:7]=[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[CH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)([O-])=O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[CH:19]1[C:10]2[CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:8](=[CH:7][C:6]3[CH:5]=[C:4]([NH2:1])[CH:25]=[CH:24][CH:23]=3)[C:9]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 59770292HCID 59770292, compound

Product 1

HCID 68940820HCID 68940820, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 5-(3-nitro-benzylidene)-5H-dibenzo[a,d]cycloheptene (120 mg, 0.4 mmol) in absolute ethanol. Add (10 ml tin chloride (416 mg, 2.0 mmol) and heat to reflux. After 18 h, cool and partition between 1N NaOH/EtOAc. Dry the organic layers (MgSO4) and concentrate to give 92.3 mg of a white solid. MS [EI+] 296 (M+H).

Workup

  1. temperatureheat to reflux
  2. temperaturecool
  3. custompartition between 1N NaOH/EtOAc
  4. dry with materialDry the organic layers (MgSO4)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b0bdf7bb447e4959a36aa53969773ed6
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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