Water → HCID 21612517, compound

HRID 1406315Notes

Reaction equation

HRID 1406315 reaction equation
[Br:1][C:2]1[N:6]=[C:5](SC)[S:4][N:3]=1.[CH:9]1C=C(Cl)C=C(C(OO)=O)C=1.[S:20]([O-:23])([O-])=[O:21].[Na+].[Na+].O>ClCCl>[Br:1][C:2]1[N:6]=[C:5]([S:20]([CH3:9])(=[O:23])=[O:21])[S:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 27612863-Bromo-5-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 21612517HCID 21612517, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-5-methylsulfanyl-[1,2,4]thiadiazole (0.8 g, 3.8 mmol) in dichloromethane (20 mL) was added dropwise mCPBA (1.97 g, 11.4 mmol) in DCM (10 mL) at 0° C. After addition, the resulting mixture was stirred at room temperature overnight. TLC (Petroleum ether:EtOAc 10:1) indicated the reaction was completed. The reaction mixture was added excess sodium sulfite and water (50 mL) to decompose the excess mCPBA. The mixture was separated and the separated organic layer was washed with brine (50 mL×3), dried over sodium sulfate and concentrated in vacuo to give residue, which was purified by a silica gel column to yield the title compound (0.58 g, 63.2%) as a white solid.

Workup

  1. additionAfter addition
  2. customThe mixture was separated
  3. washthe separated organic layer was washed with brine (50 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give residue, which
  7. customwas purified by a silica gel column

Sources & evidence

ORD record
ord-6fc86517ba1e46a09f6f22ae087a87d1
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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