6-Chloro-2,3-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1,4-trione → HCID 68182946, compound

HRID 1615581Notes

Reaction equation

HRID 1615581 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[NH:7][CH2:6][C:5](=[O:13])[C:4]=2[CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[Mg]Br>C1COCC1>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:11])(=[O:12])[NH:7][CH2:6][C:5]([C:16]3[CH:15]=[CH:14][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)([OH:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 166399256-Chloro-2,3-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1,4-trioneHCID 178418423HCID 178418423, compound

Product 1

HCID 68182946HCID 68182946, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-chloro-2,3-dihydro-4H-thieno[3,2-e][1,2]thiazin-4-one 1,1-dioxide (0.800 g, 3.36 mmol) was dissolved in THF (30 mL) and 2-naphthylmagnesium bromide (0.5 M in THF, 33.6 mL, 16.8 mmol) was added. The solution was stirred at room temperature overnight. Reaction was quenched by addition of MeOH (20 mL) and evaporated. The residue was purified using column chromatography on silica gel (80 g Analogix column, gradient 10% EA in hexane to 40% EA in hexane over 20 minutes) to give the title compound (235 mg, 18%). LCMS (FA) ES−: 364, 366. 1H NMR (400 MHz, DMSO) δ 8.46-8.42 (m, 1H), 7.97-7.89 (m, 4H), 7.55-7.52 (m, 2H), 7.35-7.32 (m, 1H), 6.74 (s, 1H), 6.63 (s, 1H), 3.90-3.84 (m, 1H), 3.69-3.64 (m, 1H).

Workup

  1. customReaction
  2. customwas quenched by addition of MeOH (20 mL)
  3. customevaporated
  4. customThe residue was purified
  5. customon silica gel (80 g Analogix column, gradient 10% EA in hexane to 40% EA in hexane over 20 minutes)

Sources & evidence

ORD record
ord-08489e07fd334beab48e084dc4b25a34
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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