Diethyl Ether → HCID 86756086, compound

HRID 1274563Notes

Reaction equation

HRID 1274563 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=O)[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]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:34])[C:17]=3[CH:35]=2)[C:3]1=[O:36].C(=O)([O-])O.[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1.C(OCC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[S:51])[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]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:34])[C:17]=3[CH:35]=2)[C:3]1=[O:36]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 70098855HCID 70098855, compound

Product 1

HCID 86756086HCID 86756086, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-{{2-{5-[3,6-dihydro-3-methyl-4-(trifluoromethyl)-2,6-dioxo-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}-p-tolyl}oxy}propionate (2.00 g, 3.80 mmol), sodium hydrogen carbonate (1.24 g, 14.8 mmol) and Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 1.70 g, 4.20 mmol) in toluene is refluxed for two hours, filtered to remove solids, and concentrated in vacuo to obtain an orange foam. Column chromatography of the foam using silica gel, and 0% and 1% diethyl ether in methylene chloride solutions gives the title product as an orange foam (1.45 g, mp 110-112° C.) which is identified by NMR spectral analyses.

Workup

  1. temperatureis refluxed for two hours
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationconcentrated in vacuo
  5. customto obtain an orange foam

Sources & evidence

ORD record
ord-8fb85f83366b40839cfab64653a5bc19
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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