Iodine → HCID 57597867, compound

HRID 1931341Notes

Reaction equation

HRID 1931341 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-9514e696e20f4752b7e499b0dd601434
Source dataset
uspto-grants-2012_05
Patent number
US08188281B2

Reaction notes

Loading…