Potassium Iodide → HCID 21883979, compound

HRID 722276Notes

Reaction equation

HRID 722276 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]1[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]1[NH:23][C:24](=[O:27])[CH2:25]Cl)=[O:12])=[CH:5]2.[I-:28].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]1[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]1[NH:23][C:24](=[O:27])[CH2:25][I:28])=[O:12])=[CH:5]2

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 21883970HCID 21883970, compound

Product 1

HCID 21883979HCID 21883979, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloro-N-{1-[(chloroacetyl)amino]-2,3-dihydro-1H-inden-2-yl}-1H-indole-2-carboxamide (Method 7; 2.0 g, 5.0 mmol) and potassium iodide (2.0 g, 12.0 mmol) in acetone (50 mL) was heated at reflux for 6 hours and then cooled and the volatiles removed by evaporation under reduced pressure. The residue was dissolved in EtOAc (50 mL) washed with IM aqueous sodium thiosulphate (2×25 mL), water (25 mL), brine (25 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure to give the title compound (2.3 g, 92%) as a pale yellow powder.

Workup

  1. temperatureat reflux for 6 hours
  2. temperaturecooled
  3. customthe volatiles removed by evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (50 mL)
  5. washwashed with IM aqueous sodium thiosulphate (2×25 mL), water (25 mL), brine (25 mL)
  6. dry with materialdried (MgSO4)
  7. customthe volatiles removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2c1e8019d2f548c098c881c0c8f38fe9
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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