Diethyl Ether → HCID 18980146, compound

HRID 2392644Notes

Reaction equation

HRID 2392644 reaction equation
C(NC(C)C)(C)C.C[Li].CCOCC.[C:15]1([S:21]([CH3:24])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CON(C)[C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[C:31]([CH3:36])[CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:15]1([S:21]([CH2:24][C:28](=[O:37])[C:29]2[CH:34]=[CH:33][C:32]([Br:35])=[C:31]([CH3:36])[CH:30]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 7912DiisopropylamineHCID 10340Sodium CarbonateHCID 18369Methyl phenyl sulfoneHCID 218337954-bromo-N-methoxy-N,3-dimethylbenzamideHCID 178418348HCID 178418348, compound

Product 1

HCID 18980146HCID 18980146, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred solution of diisopropylamine (3.6 ml, 0.026 mole) in dry THF (60 ml) at -60° C. under argon was treated with 1.5M methyllithium in ether (15.3 ml, 0.023 mole). After 15 minutes, the solution was treated dropwise over 5 minutes with a solution of methyl phenyl sulphone (2.8 g, 0.020 mole) in dry THF (20 ml). The mixture was kept at -60° C. for a further 10 minutes, then treated with a solution of N-methoxy-N-methyl-4-bromo-3-methylbenzamide (D41, 4.4 g, 0.017 mole) in dry THF (30 ml) and allowed to warm to room temp. over 1.5 h. The reaction mixture was treated with 10% Na2CO3 solution (70 ml), then concentrated in vacuo to approx. 100 ml volume and extracted with ethyl acetate (2×100 ml). The combined extract was dried and concentrated in vacuo to afford the title compound as a pale orange solid (6.0 g, 100%).

Workup

  1. waitThe mixture was kept at -60° C. for a further 10 minutes
  2. temperatureto warm to room temp. over 1.5 h
  3. concentrationconcentrated in vacuo to approx. 100 ml volume
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. extractionThe combined extract
  6. customwas dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef95debd0d2f493f9bb71cac83d84ca9
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

Loading…