Methyl morpholine oxide → HCID 86643342, compound

HRID 1948340Notes

Reaction equation

HRID 1948340 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]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 59406847Ethyl 5-(bromomethyl)-2-chloro-4-thiazolecarboxylate2×

Product 1

HCID 86643342HCID 86643342, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. customdried over molecular sieves
  2. additionwas added in a single portion
  3. concentrationThe reaction was concentrated to a solid residue
  4. dissolutionredissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialDried the organic over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customNo further purification

Sources & evidence

ORD record
ord-fd1c116058294361a355450ad5eb43ad
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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