m-Chloroperbenzoic acid → HCID 18707473, compound

HRID 619345Notes

Reaction equation

HRID 619345 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:6][N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>ClCCl>[CH3:1][S:2]([C:3]1[S:4][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:6][N:7]=1)=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18707479HCID 18707479, compound

Product 1

HCID 18707473HCID 18707473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methylsulfanyl-5-naphthalen-2-yl-[1,3,4]thiadiazole (1.3 g, 5.03 mmol) in dichloromethane (50 ml) was added 50% moisten 3-chloro peroxybenzoic acid (1.9 g, 5.53 mmol) at 0° C. After stirred for 1 h at 0° C. the reaction was diluted with dichloromethane (50 ml) and quenched with addition of saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase was separated and washed with water (50 ml), dried (MgSO4), filtered and evaporated in vacuo. The residue (1.4 g) was purified by column chromatography on silicagel (400 ml) using a mixture of ethyl acetate and heptane (1:1) as eluent. This afforded after drying in vacuo at 50° C. 0.9 g (65%) of the title compound as a solid.

Workup

  1. customquenched with addition of saturated aqueous sodium hydrogen carbonate (50 ml)
  2. customThe organic phase was separated
  3. washwashed with water (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue (1.4 g) was purified by column chromatography on silicagel (400 ml)
  8. additiona mixture of ethyl acetate and heptane (1:1) as eluent
  9. customThis afforded
  10. customafter drying in vacuo at 50° C

Sources & evidence

ORD record
ord-a7895b997d27483896ee1beca3692f80
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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