Water → HCID 11195852, compound

HRID 394840Notes

Reaction equation

HRID 394840 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-2e94cca97a114b6595dafd7f7c165fdf
Source dataset
uspto-grants-2003_08
Patent number
US06603017B2

Reaction notes

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