1,2-Dichloroethane → HCID 131720862, compound

HRID 399068Notes

Reaction equation

HRID 399068 reaction equation
[CH3:1]N(C)C(=O)C(C)C.S(O[S:17]([C:20](F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.N1C(C)=CC(C)=CC=1C.ClC1(Cl)[C:37](=[O:38])[C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:35]1[C:45]1[CH:50]=[CH:49][C:48]([S:51][CH3:52])=[CH:47][CH:46]=1.Cl[CH2:55][CH2:56]Cl>>[CH3:1][C:55]1([CH3:56])[C@@H:35]([C:45]2[CH:50]=[CH:49][C:48]([S:51][CH3:52])=[CH:47][CH:46]=2)[C@H:36]([C:39]2[CH:44]=[CH:43][C:42]([S:17][CH3:20])=[CH:41][CH:40]=2)[C:37]1=[O:38]

Participants

6

Reactant 5

HCID 111,2-Dichloroethane2×HCID 79532,4,6-TrimethylpyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 243415N,N,2-trimethylpropanamideHCID 17881582HCID 17881582, compound

Product 1

HCID 131720862HCID 131720862, compound

Procedure

To a solution of N,N-dimethyl-2-methylpropionamide (615 mg) in 1,2-dichloroethane (20 mL) at 0° C. was added triflic anhydride (1.51 g) dropwise followed by a solution of 2,4,6-collidine (715 mg) and (E)-1-(methylthio)-4-(2-phenylethenyl)benzene (730 mg, method 1) in 1,2-dichloroethane (5 mL). The mixture was stirred at r.t. for 30 min., heated at reflux for 6 hr, cooled to r.t., and the solvent evaporated. The residue was dissolved in CCl4 (50 mL) and H2O (50 mL) and the mixture refluxed for 18 hr. The organic phase was separated, the aqueous phase extracted with CH2Cl2 (2×), the combined organic phase were dried (MgSO4) and the solvents evaporated. The resulting residue was purified by flash chromatography (silica gel; toluene) to provide title product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hr
  3. temperaturecooled to r.t.
  4. customthe solvent evaporated
  5. dissolutionThe residue was dissolved in CCl4 (50 mL)
  6. temperatureH2O (50 mL) and the mixture refluxed for 18 hr
  7. customThe organic phase was separated
  8. extractionthe aqueous phase extracted with CH2Cl2 (2×)
  9. dry with materialthe combined organic phase were dried (MgSO4)
  10. customthe solvents evaporated
  11. customThe resulting residue was purified by flash chromatography (silica gel; toluene)

Sources & evidence

ORD record
ord-eaaa6f0e6b9944cea6850cf4509c4fa8
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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