Triphenylphosphine → HCID 86634599, compound

HRID 1675331Notes

Reaction equation

HRID 1675331 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:34][C:35]1[C:39]([Cl:40])=[C:38]([CH2:41][OH:42])[S:37][N:36]=1.[C:43](O)(=[S:45])[CH3:44]>C(OCC)(=O)C.C1COCC1>[C:43]([O:42][CH2:41][C:38]1[S:37][N:36]=[C:35]([Cl:34])[C:39]=1[Cl:40])(=[S:45])[CH3:44]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 16723166(3,4-Dichloroisothiazol-5-yl)methanolHCID 178418634HCID 178418634, compound

Product 1

HCID 86634599HCID 86634599, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (50 ml) solution of 2.85 g (10.9 mmol) of triphenylphosphine was added, under ice-cooling, 2.2 g (10.9 mmol) of diisopropyl azodicarboxylate, followed by stirring for 30 minutes. To the solution was added a THF (5 ml) solution of 1.0 g (5.43 mmol) of (3,4-dichloroisothiazol-5-yl)methanol and 0.83 g (10.9 mmol) of thioacetic acid, followed by stirring at room temperature for 5 hours, to give rise to a reaction. After the completion of the reaction, ethyl acetate was added to the reaction mixture. The resulting mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to obtain 0.42 g (yield: 32%) of (3,4-dichloroisothiazol-5-yl)methyl thioacetate as a light red oily substance (refractive index: 1.5855).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 5 hours
  3. customto give rise
  4. customto a reaction
  5. additionwas added to the reaction mixture
  6. washThe resulting mixture was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-361b4fe5c1f04d3aaa38dd7b0bd04dc1
Source dataset
uspto-grants-2011_08
Patent number
US08003675B2

Reaction notes

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