Acetyl chloride → 2-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

HRID 1451976Notes

Reaction equation

HRID 1451976 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[N:10]1([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=[CH:11]1>C(Cl)Cl>[C:1]([C:11]1[N:10]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

Product 1

HCID 199667522-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of acetyl chloride (6.77 ml) in DCM (400 ml) was added tin (IV) chloride (11.14 ml) at -5° C., under nitrogen. 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (20.0 g) was then added portion-wise, keeping the temperature below 0° C. The reaction mixture was then stirred at 0° C. for 0.5 hour, at which time it was poured into ice water. The layers were separated and the aqueous phase was extracted with DCM. The combined organics were washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the etude product. Purification via flash column chromatography (silica gel, DCM) afforded 9.62 g of the product as a solid, m.p. 204°-205° C.

Workup

  1. customthe temperature below 0° C
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe combined organics were washed twice with 5% HCl (aq.)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration
  7. customgave the etude product
  8. customPurification via flash column chromatography (silica gel, DCM)

Sources & evidence

ORD record
ord-3657eebc9e4441f093c1d8d583236da9
Source dataset
uspto-grants-1997_02
Patent number
US05605925

Reaction notes

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