Iodine → HCID 57709600, compound

HRID 604475Notes

Reaction equation

HRID 604475 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17].II.[NH4+].[OH-].CN([CH:26]=[O:27])C>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:17][C:16]([NH:18][CH:26]=[O:27])=[N:15][C:7]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 807IodineHCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 2723790ThioureaHCID 117355852-(2-Furanyl)-1-phenylethanone

Product 1

HCID 57709600HCID 57709600, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Furan-2-yl-1-phenyl-ethanone (14.0 g, 75 mmol) and thiourea (11.5 g, 150 mmol) was dissolved in DMF (30 mL) and iodine (19.1 g, 75 mmol) was added. The reaction mixture was heated at 100° C. overnight, then diluted with water, made alkaline with saturated aqueous NH4OH, and extracted with ether. The organic phases were washed with water, dried over sodium sulfate, filtered, concentrated and purified by flash column chromatography using 1% ethyl acetate in hexane as eluent. Yield: 9.2 g, 45%

Workup

  1. extractionextracted with ether
  2. washThe organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-6534b0dfa4234caaa8bd9cce72582754
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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