Sodium Iodide → HCID 57617824, compound

HRID 2421847Notes

Reaction equation

HRID 2421847 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][C:13]([CH3:18])([CH2:15][CH2:16]Cl)[CH3:14])[C:5]([O:7][CH3:8])=[O:6].[I-].[Na+]>CC(=O)CC>[CH3:14][C:13]1([CH3:18])[S:12][C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[NH:1][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 67242880Methyl 3-amino-4-(4-chloro-2-methylbutan-2-ylthio)benzoate

Product 1

HCID 57617824HCID 57617824, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-amino-4-(4-chloro-2-methylbutan-2-ylthio)benzoate (3.11 g, 10.8 mmol) in 2-butanone (150 mL) was added sodium iodide (4.86 g, 32.4 mmol). The reaction was heated to 70° C. and stirred at that temperature for 16 hours. Thin layer chromatography and LCMS analysis of the reaction mixture indicated consumption of starting material. The solvent was removed under reduced pressure and the resulting red slurry was diluted with EtOAc (200 mL). The organic layer was washed with saturated aqueous NaHCO3 (100 mL) and aqueous sodium hydrosulifte (50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting solid was purified by flash column chromatography using a gradient elution of hexanes with 5-70% EtOAc to provide methyl 2,2-dimethyl-2,3,4,5-tetrahydrobenzo-[b][1,4]thiazepine-7-carboxylate (1.82 g, 7.24 mmol, 67.0% yield) as an off white solid. LCMS (+ESI) m/z=252.1 [M+H]+; 1H-NMR (CDCl3) δ 7.48-7.40 (m, 3H), 4.25-4.06 (br s, 1H), 3.88 (s, 3H), 3.25 (m, 2H), 2.00 (m, 2H), 1.33 (s, 6H).

Workup

  1. customconsumption of starting material
  2. customThe solvent was removed under reduced pressure
  3. additionthe resulting red slurry was diluted with EtOAc (200 mL)
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (100 mL) and aqueous sodium hydrosulifte (50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was purified by flash column chromatography
  8. washa gradient elution of hexanes with 5-70% EtOAc

Sources & evidence

ORD record
ord-2b288d214b2e47de8f6d1acb918dec82
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

Loading…