Water → (3,4-Dichloroisothiazol-5-yl)methyl benzoate

HRID 1675330Notes

Reaction equation

HRID 1675330 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH2:8][OH:9])[S:4][N:3]=1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[C:10]([O:9][CH2:8][C:5]1[S:4][N:3]=[C:2]([Cl:1])[C:6]=1[Cl:7])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 16723166(3,4-Dichloroisothiazol-5-yl)methanol

Product 1

HCID 23658604(3,4-Dichloroisothiazol-5-yl)methyl benzoateYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.0 g (16.3 mmol) of the above-produced (3,4-dichloroisothiazol-5-yl)methanol and 2.52 g (17.9 mmol) of benzoyl chloride were dissolved in 70 ml of toluene. Thereto was dropwise added, under ice-cooling, 1.98 g (19.6 mmol) of triethylamine. The mixture was stirred at room temperature for 3 hours. Water was added, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The resulting crystals were washed with hexane to obtain 4.1 g (yield: 87%) of (3,4-dichloroisothiazol-5-yl)methyl benzoate as colorless crystals (melting point: 79 to 80° C.).

Workup

  1. additionThereto was dropwise added, under ice-
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washThe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-eabea0dbe4404a639aeb9a1e478a5cde
Source dataset
uspto-grants-2011_08
Patent number
US08003675B2

Reaction notes

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