Sodium Iodide → HCID 35155, compound

HRID 1533468Notes

Reaction equation

HRID 1533468 reaction equation
[Br:1][CH:2]([Br:15])[C:3]1[N:8]=[C:7]([CH:9](Br)Br)[N:6]=[C:5]([CH:12]([Br:14])[Br:13])[N:4]=1.[I-].[Na+].S(=O)(O)[O-].[Na+]>CC(C)=O.C(O)(=O)C>[Br:14][CH:12]([Br:13])[C:5]1[N:4]=[C:3]([CH:2]([Br:1])[Br:15])[N:8]=[C:7]([CH3:9])[N:6]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 351561,3,5-Triazine, 2,4,6-tris(dibromomethyl)-HCID 23665763Sodium Bisulfite

Product 1

HCID 35155HCID 35155, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×

Procedure

A solution of 2,4,6-tris(dibromomethyl)-s-triazine (15 g, 23.3 mmol) in acetone (100 mL) was added to a solution of sodium iodide (150 g, 1.0 mol) in acetic acid (50 mL) and acetone (500 mL). After 10 minutes at room temperature the reaction mixture was added to sodium bisulfite (25 g) in ice water (1000 mL). The aqueous layer was extracted with ether (3×100 mL). The ether layer was dried (MgSo4), filtered, and concentrated to dryness. The crude product was crystallized first from EtOH and then from cyclohexane to give the title compound (mp 87-88.5° C.). 1H NMR (CDCL3) δ2.51 (s, 3H, CH3), 6.86 (s, 2H, CH).

Workup

  1. extractionThe aqueous layer was extracted with ether (3×100 mL)
  2. dry with materialThe ether layer was dried (MgSo4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was crystallized first from EtOH

Sources & evidence

ORD record
ord-2487a7c30fe34b199a2f28e122f7d33f
Source dataset
uspto-grants-2001_03
Patent number
US06207826B1

Reaction notes

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