Dimethyl Sulfide → HCID 69554424, compound

HRID 1826411Notes

Reaction equation

HRID 1826411 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[N+:12]([C:15]1[CH:16]=[C:17](/[C:21](/[CH2:25][CH3:26])=[CH:22]/[CH2:23]O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>ClCCl>[Cl:1][CH2:23]/[CH:22]=[C:21](/[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1)\[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 69556315HCID 69556315, compound

Product 1

HCID 69554424HCID 69554424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-chlorosuccinimide (52.3 g, 0.39 mol) in dichloromethane (1.2 l) at 0° C. was added dropwise over 20 minutes dimethylsulfide (27.9 ml, 0.38 mol). To the mixture was added dropwise over 20 minutes at 0° C. a solution of (E)-3-(3-nitrophenyl)-2-penten-1-ol (Preparation 14, 80 g, 0.39 mol) in dichloromethane (300 ml). The mixture was warmed to room temperature over 1 h, stirred at room temperature for 16 h, then partitioned between water (2 l) and dichloromethane (1 l). The layers were separated and the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica column chromatography (2 kg), eluting with 10:1 hexane/diethyl ether. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a very pale yellow oil (54 g, 62%).

Workup

  1. custompartitioned between water (2 l) and dichloromethane (1 l)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (2 kg)
  7. washeluting with 10:1 hexane/diethyl ether
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c059424688114e4e8c9b55973a47b957
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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