Iodoethane → HCID 69220617, compound

HRID 1393102Notes

Reaction equation

HRID 1393102 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([NH:14][CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH3:31])=[CH:9][C:8]=1[CH3:32])[CH3:2].[CH2:34](I)[CH3:35].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([CH2:34][CH3:35])[CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:26]=3)=[N:18][C:17]=2[CH3:31])=[CH:9][C:8]=1[CH3:32])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69218024HCID 69218024, compound

Product 1

HCID 69220617HCID 69220617, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.102 g (0.21 mmol) of the above prepared (2,6-dimethyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester was dissolved in 1.5 ml of abs. DMSO and treated with 0.066 g (0.43 mmol) of ethyl iodide and 0.032 g (0.23 mmol) of K2CO3. After vigorously stirring for 18 h at ambient temperature, the reaction mixture was poured onto crashed ice/aqueous 10% KHSO4, extracted twice with EtOAc, the organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/EtOAc=8/2), yielded finally 0.067 g of the title compound as yellow oil, MS: 507.6 (MH)+.

Workup

  1. dissolutionwas dissolved in 1.5 ml of abs
  2. additionthe reaction mixture was poured
  3. extractionextracted twice with EtOAc
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9bc987ecd8fb4eb8b9d9b1b30f44d88e
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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