Tin tetrachloride → HCID 13457762, compound

HRID 280134Notes

Reaction equation

HRID 280134 reaction equation
[C:1]1(=[O:17])[N:5]([N:6]2[CH:10]=[CH:9][CH:8]=[C:7]2[CH3:11])[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].[Sn](Cl)(Cl)(Cl)Cl>ClCCl>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([C:10]1[N:6]([N:5]2[C:4](=[O:12])[C:3]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]3[C:1]2=[O:17])[C:7]([CH3:11])=[CH:8][CH:9]=1)=[O:22]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 691102-Chlorobenzoyl chlorideHCID 23321782HCID 23321782, compound

Product 1

HCID 13457762HCID 13457762, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-phthalimido-2-methylpyrrole (105 g, 0.46 mol) and o-chlorobenzoyl chloride (162.5 g, 0.93 mol) in 1.5 liters of dichloromethane at 0° was added tin (IV) chloride (243 g, 0.94 mol) over 15 minutes. The resultant mixture was warmed to room temperature over 30 minutes and then quenched with 2 liters of H2O. The organic layer was washed with H2O and brine, dried (MgSO4), charcoaled and filtered. Evaporation of the volatiles left an oil which was purified by flash chromatography (silica, dichloromethane) to give 126 g of powder. This powder was recrystallized from ether-petroleum ether to give 82 g (48%) of powder, m.p. 260°-262°.

Workup

  1. customquenched with 2 liters of H2O
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customEvaporation of the volatiles
  6. waitleft an oil which
  7. customwas purified by flash chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-90e10ca5e7a24bcd9fb050932275b95d
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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