Sodium Iodide → HCID 86750309, compound

HRID 400292Notes

Reaction equation

HRID 400292 reaction equation
[Na+].[I-].[Si](Cl)(C)(C)C.[CH3:8][N:9]([CH3:75])[C:10]([S:12][C:13]1[C:24]2[O:23][C:22]([CH3:26])([CH3:25])[O:21][C:20]=2[C:19]([C:27]([C:51]2[C:61]3[O:62][C:63]([CH3:66])([CH3:65])[O:64][C:60]=3[C:59]([S:67][C:68]([N:70]([CH3:72])[CH3:71])=[O:69])=[C:53]3[O:54][C:55]([CH3:58])([CH3:57])[O:56][C:52]=23)([C:29]2[C:39]3[O:40][C:41]([CH3:44])([CH3:43])[O:42][C:38]=3[C:37]([S:45][C:46]([N:48]([CH3:50])[CH3:49])=[O:47])=[C:31]3[O:32][C:33]([CH3:36])([CH3:35])[O:34][C:30]=23)O)=[C:18]2[C:14]=1[O:15][C:16]([CH3:74])([CH3:73])[O:17]2)=[O:11].[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N.C(Cl)Cl>[CH3:50][N:48]([CH3:49])[C:46]([S:45][C:37]1[C:38]2[O:42][C:41]([CH3:43])([CH3:44])[O:40][C:39]=2[C:29]([CH:27]([C:19]2[C:20]3[O:21][C:22]([CH3:26])([CH3:25])[O:23][C:24]=3[C:13]([S:12][C:10]([N:9]([CH3:8])[CH3:75])=[O:11])=[C:14]3[O:15][C:16]([CH3:73])([CH3:74])[O:17][C:18]=23)[C:51]2[C:61]3[O:62][C:63]([CH3:66])([CH3:65])[O:64][C:60]=3[C:59]([S:67][C:68]([N:70]([CH3:71])[CH3:72])=[O:69])=[C:53]3[O:54][C:55]([CH3:58])([CH3:57])[O:56][C:52]=23)=[C:30]2[C:31]=1[O:32][C:33]([CH3:36])([CH3:35])[O:34]2)=[O:47]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium Thiosulfate2×HCID 86750310HCID 86750310, compound

Product 1

HCID 86750309HCID 86750309, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

NaI (1.135 g, 8.00 mmol) and Me3SiCl (1 mL, 8.0 mmol) were stirred in CH3CN (70 mL) at 0° C. Tris(8-dimethylaminocarbonylthio-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methanol (1.00 g, 0.9979 mmol (Example 43)) dissolved in CH3CN 10 mL) was added and the resulting solution stirred for 30 minutes when 1H NMR analysis of a small sample showed conversion to be complete. Na2S2O3 (sat., 30 mL) was added and the two phase system was stirred 30 minutes when more Na2S2O3 (sat. 30 mL) was added and the stirring was continued for 5 more minutes. The phases were separated and the organic layer was dried (MgSO4), filtered, the filter washed with diethyl ether (30 mL) and the solution was evaporated, yielding 1.16 g yellow to brown crystals. The crystals were dissolved in CH2Cl2, the solution was washed with NaHCO3 (30 mL, sat.) and H2O (30 mL), dried (MgSO4) and evaporated yielding 0.92 g of the pure title compound.

Workup

  1. additionwas added
  2. additionwas added
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. washthe filter washed with diethyl ether (30 mL)
  7. customthe solution was evaporated
  8. customyielding 1.16 g yellow to brown crystals
  9. washthe solution was washed with NaHCO3 (30 mL, sat.) and H2O (30 mL)
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-8cb59607388c4ff99e8c937f1c6ce161
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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