Iodine → HCID 117709797, compound

HRID 2274166Notes

Reaction equation

HRID 2274166 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=[C:11]([O:23]CC2C=CC=CC=2)[N:10]=1)C1C=CC=CC=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+].[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH2:46]([N:14]1[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:12][C:11](=[O:23])[N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:8])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 807IodineHCID 1140TolueneHCID 24477Sodium ThiosulfateHCID 2252572,4,6-tris(benzyloxy)-1,3,5-triazine

Product 1

HCID 117709797HCID 117709797, compoundYield 21%

Procedure

Furthermore, a synthesis method of the hydroxy group-protecting agent 5 will be explained. To a 10 mL eggplant flask, 599.2 mg (1.50 m mol) of 2,4,6-tribenzyloxy-1,3,5-triazine, 5.00 mL of toluene and 38.8 mg (030 m mol) of iodine were added, heat-perfused, and reacted for 31 hours. After the reaction, 5 mL of an aqueous solution of saturated sodium thiosulfate was added, which was washed with 5 mL of 1 N sodium bicarbonate water, 5 mL of 1 N hydrochloric acid, 5 mL of water and 5 mL of saturated salt water. A resulting organic phase was dried by magnesium sulfate, from which the solvent was distilled away, and the residue was isolated and purified by silica-gel chromatography to obtain 126.2 mg of 1,3-dibenzyl-6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (yield: 21%).

Workup

  1. customheat-perfused, and reacted for 31 hours
  2. additionwas added
  3. washwhich was washed with 5 mL of 1 N sodium bicarbonate water, 5 mL of 1 N hydrochloric acid, 5 mL of water and 5 mL of saturated salt water
  4. dry with materialA resulting organic phase was dried by magnesium sulfate, from which the solvent
  5. distillationwas distilled away
  6. customthe residue was isolated
  7. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-9e0afbaf25ec4d63ab680b7711a075e4
Source dataset
uspto-grants-2015_09
Patent number
US09126954B2

Reaction notes

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