Potassium Iodide → HCID 69475972, compound

HRID 1271392Notes

Reaction equation

HRID 1271392 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[N:20]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)[CH:24]=[CH:23][N:22]=[N:21]1.[I-].[K+].C[O-].[Na+]>CO>[F:18][CH:17]([F:19])[O:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[CH:8][C:5]2[O:6][CH:7]=[C:3]([CH2:2][O:35][C:32]3[CH:33]=[CH:34][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)=[CH:30][CH:31]=3)[N:4]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 691125744-(Chloromethyl)-2-{2-[4-(difluoromethoxy)phenyl]ethenyl}-1,3-oxazole

Product 1

HCID 69475972HCID 69475972, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.286 g (1.00 mmol) 4-Chloromethyl-2-[2-(4-difluoromethoxy-phenyl)-vinyl]-oxazole, 0.217 g 1.00 mmol) 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenol, 0.166 g (1.00 mmol) potassium iodide and 0.191 ml (1.00 mmol) of a 30% sodium methylate solution were added to 50.0 ml methanol and heated to reflux for 12 h. After removal of solvent, partitioning of the residue between 50 ml ethyl acetate and 15 ml water, the organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH, 15 ml water twice and dried over sodium sulphate. The solution was concentrated to a volume of 5 ml until crystallisation of the product started. After leaving for 1 h at room temperature the precipitate was sucked off, washed with ether and dried at 40° C. in vacuo. Yield 0.20 g (43%) 3.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. customAfter removal of solvent
  4. custompartitioning of the residue between 50 ml ethyl acetate and 15 ml water
  5. washthe organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH, 15 ml water twice
  6. dry with materialdried over sodium sulphate
  7. concentrationThe solution was concentrated to a volume of 5 ml until crystallisation of the product
  8. customAfter leaving for 1 h at room temperature the precipitate
  9. washwashed with ether
  10. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-b3c6824d816646d686b72dce51dc135b
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

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