Diethyl Ether → HCID 68183049, compound

HRID 1615511Notes

Reaction equation

HRID 1615511 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.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.CCOCC>C1COCC1>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:11])(=[O:12])[NH:7][CH2:6][C:5]([C:18]3[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=3)([OH:13])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 166399256-Chloro-2H-thieno[3,2-e][1,2]thiazin-4(3H)-one 1,1-dioxideHCID 178478191HCID 178478191, compound

Product 1

HCID 68183049HCID 68183049, compoundYield 26%

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 (0.820 g, 3.45 mmol) was dissolved in THF (31 mL) and 1 M of 4-Chlorophenylmagnesium bromide in ether (8.2 mL, 8.2 mmol) was added. The solution was stirred at room temperature overnight. At that time, TLC indicated good conversion. Reaction was quenched by addition of satd NaHCO3 (20 mL) and extracted with EA (3×50 mL). The combined organic extracts were washed with brine (20 mL), dried with MgSO4, filtered 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 product (0.34 g, 26%). LCMS: (FA) ES-348, 350, 352. 1H NMR (400 MHz, d6-DMSO) δ: 8.41 (dd, J=8.75, 5.76 Hz, 1H), 7.49-7.42 (m, 2H), 7.33-7.25 (m, 2H), 6.74 (s, 1H), 6.57 (s, 1H), 3.70-3.60 (m, 2H).

Workup

  1. customReaction
  2. customwas quenched by addition of satd NaHCO3 (20 mL)
  3. extractionextracted with EA (3×50 mL)
  4. washThe combined organic extracts were washed with brine (20 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified
  9. 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-80815ba3b7aa47158d86f10790ef184a
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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