Tin tetrachloride → HCID 19036964, compound

HRID 233123Notes

Reaction equation

HRID 233123 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.[CH3:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:18]=1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:18]2[N:19]([N:26]3[C:34](=[O:35])[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:36])[C:20]3[C:25]([C:17]=2[CH3:16])=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 678794-Fluorobenzoyl chlorideHCID 19036947HCID 19036947, compound

Product 1

HCID 19036964HCID 19036964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.14 ml of 4-fluorobenzoyl chloride and 450 ml of dry DCM was cooled in an ice/salt bath to 0° C. To the stirred solution was added 7.74 ml of tin (IV) chloride. The mixture was stirred at -5° C. to 0° C. for 10 minutes after which was added 18.0 g of 2-[(3-methyl-1H-indol-1-yl]-1H-isoindole-1,3-(2H)dione (Example 10b). The reaction mixture was stirred at 0° C. for 1.5 hours, allowed to warm to room temperature for 2 hours, cooled again in an ice bath, poured onto ice, extracted twice with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated to a yellow solid. Chromatography (15% acetone/heptane) provided a solid weighing 56.8 g. Recrystallization from ethyl alcohol gave 21.1 g of the product, m.p. 227°-228° C.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1.5 hours
  2. temperaturecooled again in an ice bath
  3. additionpoured onto ice
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a yellow solid
  9. customChromatography (15% acetone/heptane) provided a solid
  10. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-0f470bf33ead42f28f877e949010aed1
Source dataset
uspto-grants-1997_01
Patent number
US05591866

Reaction notes

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