Lawesson's reagent → HCID 86650271, compound

HRID 221764Notes

Reaction equation

HRID 221764 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][O:12][CH2:11][C:10](=O)[NH:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][O:12][CH2:11][C:10](=[S:29])[NH:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 666659335-(2-Fluoro-phenyl)-5-trifluoromethyl-[1,4]oxazepan-3-one

Product 1

HCID 86650271HCID 86650271, compoundYield 180.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-fluoro-phenyl)-5-trifluoromethyl-[1,4]oxazepan-3-one (1.19 g, 4.29 mmol) in 15 mL THF was added Lawesson's reagent (955 mg, 2.36 mmol). The reaction mixture was stirred at room temperature over night. The mixture was then partitioned between aqueous Na2CO3 solution (2 mol/L) and TBME. The layers were separated, washed with aqueous Na2CO3 solution (2 mol/L), brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/EtOAc 95/5->90/10 to give 1.25 g of the title compound as a yellow resin.

Workup

  1. customThe mixture was then partitioned between aqueous Na2CO3 solution (2 mol/L) and TBME
  2. customThe layers were separated
  3. washwashed with aqueous Na2CO3 solution (2 mol/L), brine and TBME
  4. dry with materialThe combined organic layers were dried over MgSO4.H2O
  5. customevaporated
  6. customThe crude product was purified on a silica gel column
  7. washby eluting with hexane/EtOAc 95/5->90/10

Sources & evidence

ORD record
ord-a3ca7418e6484e2e9b7f42cbae1cdb81
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

Loading…