Sodium Iodide → HCID 18943063, compound

HRID 400287Notes

Reaction equation

HRID 400287 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.[CH3:8][C:9]([S:11][C:12]1[C:23]2[O:22][C:21]([CH3:25])([CH3:24])[O:20][C:19]=2[C:18]([C:26]([C:48]2[C:58]3[O:59][C:60]([CH3:63])([CH3:62])[O:61][C:57]=3[C:56]([S:64][C:65]([CH3:67])=[O:66])=[C:50]3[O:51][C:52]([CH3:55])([CH3:54])[O:53][C:49]=23)([C:28]2[C:38]3[O:39][C:40]([CH3:43])([CH3:42])[O:41][C:37]=3[C:36]([S:44][C:45]([CH3:47])=[O:46])=[C:30]3[O:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=23)O)=[C:17]2[C:13]=1[O:14][C:15]([CH3:69])([CH3:68])[O:16]2)=[O:10]>C(#N)C>[CH3:67][C:65]([S:64][C:56]1[C:50]2[O:51][C:52]([CH3:54])([CH3:55])[O:53][C:49]=2[C:48]([CH:26]([C:18]2[C:19]3[O:20][C:21]([CH3:25])([CH3:24])[O:22][C:23]=3[C:12]([S:11][C:9]([CH3:8])=[O:10])=[C:13]3[O:14][C:15]([CH3:68])([CH3:69])[O:16][C:17]=23)[C:28]2[C:38]3[O:39][C:40]([CH3:42])([CH3:43])[O:41][C:37]=3[C:36]([S:44][C:45]([CH3:47])=[O:46])=[C:30]3[O:31][C:32]([CH3:34])([CH3:35])[O:33][C:29]=23)=[C:58]2[C:57]=1[O:61][C:60]([CH3:63])([CH3:62])[O:59]2)=[O:66]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86750305HCID 86750305, compound

Product 1

HCID 18943063HCID 18943063, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NaI (0.15972 g, 1.1256 mmol) and trimethylsilyl chloride (0.142 mL, 1.1256 mmol) were stirred in acetonitrile (50 mL). Tris(8-methylcarbonylthio-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol (0.1286 g, 0.1407 mmol, Example 49) was added in solid form and the color of the solution became brownish. Na2S2 O4 (20 mL, sat.) was added after 60 minutes and the mixture was stirred 5 minutes before separation of the phases. The aqueous phase was extracted with diethyl ether (50 mL), and the combined organic phase was dried (MgSO4) and evaporated, yielding 0.105 g (0.1168 mmol, 83%) of the title compound.

Workup

  1. addition(20 mL, sat.) was added after 60 minutes
  2. extractionThe aqueous phase was extracted with diethyl ether (50 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f34f8e4aaab042e59af07b66dffb3bee
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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