Ethyl Acetate → N-(7-Bromo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 539367Notes

Reaction equation

HRID 539367 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].CCOC(C)=O.C([O-])(O)=O.[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[N:19][S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 516892Sodium BicarbonateHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 67979348N-(7-Bromo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-methylpropane-2-sulfinamideYield 100%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 962WaterSolvent

Procedure

7-Bromo-3,4-dihydronaphthalen-1(2H)-one (5 g, 22.21 mmol), 2-methylpropane-2-sulfinamide (4.04 g, 33.32 mmol) and titanium ethoxide (9.15 mL, 44.43 mmol) were dissolved in 2-Me THF (50 mL) and heated to reflux for 22 h. The reaction was left to cool down to r.t. EtOAc (20 mL), NaHCO3 (sat, 5 mL) and water was added under stirring. The mixture was left to stand without stirring for 1 h. The organic phase was collected by filtration, dried over MgSO4 and concentrated in vacuo to give the title compound (7.29 g) that was used without purification in the next step: 1 H NMR (500 MHz, CDCl3) δ ppm 1.34 (s, 9 H), 2.00-2.10 (m, 2 H), 2.77-2.86 (m, 2 H), 3.01-3.12 (m, 1 H), 3.28 (ddd, 1 H), 7.09 (d, 1 H), 7.50 (dd, 1 H), 8.25 (d, 1 H), MS (ES+) m/z 328[M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 22 h
  3. waitThe reaction was left
  4. waitThe mixture was left
  5. stirringwithout stirring for 1 h
  6. filtrationThe organic phase was collected by filtration
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dca2661a885441739d863653c1bdda2f
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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