Iodine → 1,9-Dimethylphenothiazin-5-ium iodide

HRID 72815

Reaction equation

HRID 72815 reaction equation
[CH3:1][C:2]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[CH3:16])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[I:17]I>C(Cl)(Cl)Cl>[I-:17].[CH3:16][C:12]1[C:13]2[C:8](=[S+:7][C:6]3[C:15]([N:14]=2)=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=3)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 807IodineHCID 674644911,9-dimethyl-10H-phenothiazine

Product 1

HCID 890773051,9-Dimethylphenothiazin-5-ium iodide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1,9-Dimethylphenothiazine (4.2026 g, 18.49 mmol) was dissolved in 130 mL of chloroform and crushed iodine (14.1 g, 55.55 mmol, 3 eq.) dissolved in 520 mL of chloroform was added over 2 hurs. Once newly formed precipitate was filtered off or the solvent removed under vacuum, the resulting iodide salt was stirred with ether or hexane (sometimes overnight) to remove excess iodine then refiltered. After pumping down under vacuum, a brown precipitate was obtained as product (12.6 g).

Workup

  1. additionwas added over 2 hurs
  2. filtrationOnce newly formed precipitate was filtered off
  3. customthe solvent removed under vacuum
  4. customto remove excess iodine
  5. customa brown precipitate was obtained as product (12.6 g)

Sources & evidence

ORD record
ord-cedc4d50e13a4c5098b83e0fbcb6f8ee
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Linked notes

Loading…