Diethyl Ether → HCID 13910802, compound

HRID 1252198Notes

Reaction equation

HRID 1252198 reaction equation
[N+]([O-])([O-])=O.[IH2+:5].[CH3:6][N:7]([CH3:19])[C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:11]=[CH:12][CH:13]=1.CCOCC.C(Cl)(Cl)[Cl:26]>>[ClH:26].[CH3:19][N:7]([CH3:6])[C:8]1[CH:13]=[CH:12][C:11]([I:5])=[C:10]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:9]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 13910799HCID 13910799, compoundHCID 20141152HCID 20141152, compound

Product 1

HCID 13910802HCID 13910802, compound

Procedure

A solution of 0.16 moles of iodonium nitrate in 280 ml of CHCl3 was added to 30.4 g of 4-(3-dimethylaminophenyl)-2-butanone. The mixture was stirred for 2 hr. Ether was added and the precipitated solid was removed by filtration. The solvent was evaporated in vacuo. The residue was partitioned between water and ether. The ether solution was washed with sodium thiosulfate solution and brine. The solution was dried (K2CO3) and the solvent evaporated. The residue was taken up in ether and ethereal hydrogen chloride added. The precipitate (47.4 g, 85% yield) of the title compound was collected mp 120°-121° C.

Workup

  1. customthe precipitated solid was removed by filtration
  2. customThe solvent was evaporated in vacuo
  3. customThe residue was partitioned between water and ether
  4. washThe ether solution was washed with sodium thiosulfate solution and brine
  5. dry with materialThe solution was dried (K2CO3)
  6. customthe solvent evaporated
  7. additionethereal hydrogen chloride added

Sources & evidence

ORD record
ord-aca1a09e8d4d437ebbfe6b25b361a3e5
Source dataset
uspto-grants-1988_05
Patent number
US04742084

Reaction notes

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