Tin tetrachloride → HCID 13457762, compound

HRID 462758Notes

Reaction equation

HRID 462758 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 temperatue 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-d32996cc492d4151ab8f50625b3dc6e9
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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