Diisopropyl Ether → HCID 86681580, compound

HRID 339433Notes

Reaction equation

HRID 339433 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([C:26](=[N:36][O:37][CH:38]([CH3:40])[CH3:39])[C:27]([N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[N:28][O:29][CH3:30])(=O)[NH2:24].C(OC(C)C)(C)C>O1CCCC1>[CH:38]([O:37][N:36]=[C:26]([C:23](=[S:10])[NH2:24])[C:27]([N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[N:28][O:29][CH3:30])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 87949Lawesson's reagentHCID 86681581HCID 86681581, compound

Product 1

HCID 86681580HCID 86681580, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

0.77 g (1.9 mmol) of Lawesson's reagent was added, at room temperature, to a tetrahydrofuran (8 ml) solution containing 0.40 g (1.6 mmol) of 1-(2-carbamoyl-2-isopropoxyimino-1-methoxyiminoethyl)-1H-1,2,4-triazole, followed by stirring at 40° C. for 2 hours and then at 60° C. for 3 hours. The reaction mixture was cooled to room temperature. Thereto was added diisopropyl ether. The mixture was washed with water and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2) to obtain 0.25 g (yield: 58%) of a title compound as a yellow powder.

Workup

  1. waitat 60° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washThe mixture was washed with water
  4. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-9ff50796735d4081b840f9eeea47d211
Source dataset
uspto-grants-2014_11
Patent number
US08895035B2

Reaction notes

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