Potassium Iodide → HCID 15789767, compound

HRID 1653964Notes

Reaction equation

HRID 1653964 reaction equation
[Cl:1][C:2]1[C:7]([SH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[C:12]3[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.Cl[CH2:22][C:23]([O:25][CH:26]1[CH:30]([O:31][C:32](=[O:34])[CH3:33])[CH2:29][O:28][CH2:27]1)=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:32]([O:31][CH:30]1[CH2:29][O:28][CH2:27][CH:26]1[O:25][C:23]([CH2:22][S:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:20])=[C:5]([N:9]2[C:10](=[O:19])[C:11]3[CH2:18][CH2:17][CH2:16][CH2:15][C:12]=3[C:13]2=[O:14])[CH:6]=1)=[O:24])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13563760HCID 13563760, compoundHCID 15745726HCID 15745726, compound

Product 1

HCID 15789767HCID 15789767, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 14.0 g of N-(4-chloro-2-fluoro-5-mercaptophenyl)-3,4,5,6-tetrahydrophthalimide, 11.0 g of 4-acetoxytetrahydrofuran-3-yl chloroacetate, 7.46 g of potassium carbonate, 1.5 g of potassium iodide and 150 ml of acetone was refluxed under stirring for 5 hours. After cooling, the salt was filtered off, and the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3), to obtain 14.5 g of a compound described in Table 1 (No. 6) (65%).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. filtrationthe salt was filtered off
  4. customthe residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3)

Sources & evidence

ORD record
ord-932f4781fc9740a68b59f9dcfeccf89a
Source dataset
uspto-grants-1995_04
Patent number
US05405828

Reaction notes

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