Iodine → HCID 57597867, compound

HRID 1024399Notes

Reaction equation

HRID 1024399 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:12]=2)=[CH:7][C:4]=1[CH:5]=O.[OH-].[NH4+:31].II>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:12]=2)=[CH:7][C:4]=1[C:5]#[N:31]

Participants

6

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 57598046HCID 57598046, compound

Product 1

HCID 57597867HCID 57597867, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The aldehyde 36 (98 mg, 241 μmol) was dissolved in tetrahydrofuran (5 ml). To this was added 30% aqueous ammonium hydroxide (3 ml) and iodine (79 mg, 313 μmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and extracted with ether and ethyl acetate. The organics were washed with aqueous sodium sulfite (50 mg) in water (10 ml). The organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give 37 (95.8 mg, 98%).

Workup

  1. extractionextracted with ether and ethyl acetate
  2. washThe organics were washed with aqueous sodium sulfite (50 mg) in water (10 ml)
  3. washThe organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-017cb3eed3ca4e5887d9743b929049aa
Source dataset
uspto-grants-2014_05
Patent number
US08722889B2

Reaction notes

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