Water → HCID 11195852, compound

HRID 2084622Notes

Reaction equation

HRID 2084622 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5](Cl)=[CH:6][CH:7]=1.[CH3:15][S-:16].[Na+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5]([S:16][CH3:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 11333689HCID 11333689, compound

Product 1

HCID 11195852HCID 11195852, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

20 g (0.083 mol) of 3-(3,6-dichloro-2-methylphenyl)-4,5-dihydroisoxazole are dissolved in 120 ml of NMP. At 0° C., 6.7 g (0.09 mol) of sodium thiomethoxide are added over a period of 40 min, and the mixture is then stirred overnight. The reaction mixture is stirred into 360 ml of water and extracted four times with 70 ml of toluene, the combined organic phases are washed once with 70 ml of water and the organic phase is concentrated. The residue (an isomer mixture) is distilled at 150-170° C. under a reduced pressure of 1 mbar. The main fraction is purified chromatographically. This gives 4.5 g of a product which is 83% pure (17% of theory).

Workup

  1. extractionextracted four times with 70 ml of toluene
  2. washthe combined organic phases are washed once with 70 ml of water
  3. concentrationthe organic phase is concentrated
  4. distillationThe residue (an isomer mixture) is distilled at 150-170° C. under a reduced pressure of 1 mbar
  5. customThe main fraction is purified chromatographically

Sources & evidence

ORD record
ord-9eb0b6db0bdd4d73b5246899fd9403ba
Source dataset
uspto-grants-2004_04
Patent number
US06716989B2

Reaction notes

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