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

HRID 411215Notes

Reaction equation

HRID 411215 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) δ 3.40, 4.20, 7.53; IR (diffuse reflectance) 2986, 1675, 1664, 1505, 1478, 1405, 1338, 1327, 1275, 1245, 1177, 1158, 1129, 818, 781 cm−1; 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-fb513309bdb744a6b7d38b7267ff2770
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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