Methyl morpholine oxide → HCID 86643342, compound
Reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][C:4]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C[N+]1([O-])CC[O:18]CC1>C(#N)C>[Cl:8][C:6]1[S:7][C:3]([CH:2]=[O:18])=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 5-(bromomethyl)-2-chloro-1,3-thiazole-4-carboxylate (Intermediate 180, 920 mg; 3.2 mmol) was dissolved in acetonitrile dried over molecular sieves. The solution was cooled to 0 C and NMO (570 mg; 1.5 equiv.) was added in a single portion. The reaction was monitored by LC/MS. An additional 1.5 equivalents of NMO was added in two portions over two hours. The reaction was concentrated to a solid residue, redissolved in EtOAc and washed with H2O. Dried the organic over Na2SO4, filtered and concentrated. No further purification. MS (ES) MH+: 220, 222 for C7H6ClNO3S.