Sodium Iodide → HCID 66748108, compound

HRID 1747921Notes

Reaction equation

HRID 1747921 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1.[O:16]=[S:17]1(=[O:34])[CH2:22][CH2:21][N:20]2[CH:23]=[CH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:19]2=[N:18]1>CS(C)=O.O>[O:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[CH2:10][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]2[C:19]3=[N:18][S:17](=[O:34])(=[O:16])[CH2:22][CH2:21][N:20]3[CH:23]=[CH:24][CH:25]=2)=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66748108HCID 66748108, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of potassium carbonate (450 mg), sodium iodide (488 mg), 2-(bromomethyl)tetrahydrofuran (538 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (10 mL) was stirred at 130° C. for 5 hr. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was washed with IPE to give the title compound (332 mg) as a pale yellow solid. The solid was crystallized from CH3CN-IPE to give a pale yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with IPE

Sources & evidence

ORD record
ord-6913e91e9fc94c2cb26cb38c06718819
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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