Diethyl Ether → HCID 86756087, compound

HRID 1274568Notes

Reaction equation

HRID 1274568 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH:28]([CH3:32])[C:29]([OH:31])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:33])[C:17]=3[CH:34]=2)[C:3]1=[O:35].C(Cl)(=O)C(Cl)=O.[CH2:42](O)[C:43]#[CH:44].C(OCC)C>C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH:28]([CH3:32])[C:29]([O:31][CH2:44][C:43]#[CH:42])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:33])[C:17]=3[CH:34]=2)[C:3]1=[O:35]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7859Propargyl alcoholHCID 65578Oxalyl chlorideHCID 70096977HCID 70096977, compound

Product 1

HCID 86756087HCID 86756087, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A mixture of 2-{{2-{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}-p-tolyl}oxy}propionic acid (0.510 g, 1.00 mmol) and oxalyl chloride (0.380 g, 3.00 mmol) in methylene chloride is stirred at room temperature for 30 minutes and concentrated in vacuo to obtain a yellow foam. The foam is diluted with methylene chloride and the resultant solution is treated with a solution of propargyl alcohol (0.110 g, 2.00 mmol) in methylene chloride, stirred at room temperature for 24 hours, and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel, a hexanes/methylene chloride solution (1:1) and a 5% diethyl ether in methylene chloride solution gives the title product (0.400 g) which is identified by NMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a yellow foam
  3. stirringstirred at room temperature for 24 hours
  4. concentrationconcentrated in vacuo
  5. customto obtain an oil

Sources & evidence

ORD record
ord-938c9422fd944618a0d01f36fe4f942b
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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