Dimethylformamide → HCID 18752856, compound

HRID 989251Notes

Reaction equation

HRID 989251 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.CN(C)C=O.[Cl:19]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[Cl:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 8166855-bromo-7-nitroindole

Product 1

HCID 18752856HCID 18752856, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12.00 g (49.8 mmol) of 5-bromo-7-nitro-1H-indole in 140 ml of tetrahydrofuran were added 1.4 ml of dimethylformamide and 6.98 g (52.3 mmol) of N-chlorosuccinimide followed by stirring at room temperature overnight. A 10% aqueous solution of sodium thiosulfate was added thereto followed by extracting with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated to dryness to give 14.84 g of the title compound.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5a3d013a806e4b1aad759a3841241a88
Source dataset
uspto-grants-2003_10
Patent number
US06638964B2

Reaction notes

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