Sodium Iodide → HCID 66649247, compound

HRID 418746Notes

Reaction equation

HRID 418746 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=3)[S:13][C:6]=12.Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=3)[S:13][C:6]=12

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 59424530HCID 59424530, compound

Product 1

HCID 66649247HCID 66649247, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a flask containing a suspension of 419 (0.299 g, 0.753 mmol) in acetonitrile (8 mL) was added chlorotrimethylsilane (0.095 mL, 0.748 mmol) followed by sodium iodide (0.112 g, 0.748 mmol). The mixture was then heated to between 70 to 100° C. over 24 hours. Over this time four additional portions of chlorotrimethylsilane (0.095 mL each portion) and sodium iodide (0.112 g each portion) were added. The reaction mixture was then cooled to room temperature and the formed precipitate was collected by filtration, washed with NH4OH and water, and dried to provide title compound 420 as a brown solid (0.283 g, 98%). MS (m/z): 284.0 (M+H), 406.0 (M+Na).

Workup

  1. additionTo a flask containing
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationthe formed precipitate was collected by filtration
  4. washwashed with NH4OH and water
  5. customdried

Sources & evidence

ORD record
ord-05c5d544e70546fea96129eb16ff67e7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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