Iodine → 6-iodo-1-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

HRID 1070631Notes

Reaction equation

HRID 1070631 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:11])[CH2:4][S:3]1(=[O:13])=[O:12].[I:14]I>C(Cl)(Cl)Cl>[I:14][C:9]1[S:8][C:7]2[N:2]([CH3:1])[S:3](=[O:13])(=[O:12])[CH2:4][C:5](=[O:11])[C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 807IodineHCID 223971671-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

Product 1

HCID 223971566-iodo-1-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxideYield 43.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 1-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide (Preparation 33, 1.0 g) in CHCl3 (100 ml) at ambient temperature is added HgO (1.19 g) and iodine (1.17 g). The resulting mixture is stirred overnight at ambient temperature and the solids removed by filtration through diatomaceous earth. The solvent is removed in vacuo and the residue purified via flash column chromatography (4/1, hexanes/EtOAc) to afford 0.68 g (43%) of the title compound as a tan solid. Physical characteristics: 1H NMR (CDCl3) δ3.40, 4.20, 7.53; IR (diffuse reflectance) 2986, 1675, 1664, 1505, 1478, 1405, 1338, 1327, 1275, 1245, 1177, 1158, 1129, 818, 781 cm1; MS (EI) m/z 343 (M+). Anal. Found: C, 24.65; H, 1.82; N, 4.08.

Workup

  1. customthe solids removed by filtration through diatomaceous earth
  2. customThe solvent is removed in vacuo
  3. customthe residue purified via flash column chromatography (4/1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-a0a30a6dbe5b43afbb2be75b2d4c2327
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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