m-Chloroperbenzoic acid → HCID 20026533, compound

HRID 1382727Notes

Reaction equation

HRID 1382727 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[N:6]=1)[CH2:2][CH3:3].C(=O)(O)[O-:23].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[O:23])[N:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 20026534HCID 20026534, compound

Product 1

HCID 20026533HCID 20026533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 710 mg. (2.38 m mole) of 8-(4-n-propoxy-2-pyrimidylthio)quinoline and 999 mg. of sodium bicarbonate (11.9 m mole) in 40 ml. of methylene chloride cooled to 0° C. was added dropwise over a period of 15 minutes 574 mg. (3.33 m mole) of m-chloroperbenzoic acid in 15 ml. of the same solvent. The reaction mixture was stirred for 30 minutes and was then allowed to warm to room temperature and stirred overnight. The reaction was diluted with methylene chloride and the organic layer washed successively with a saturated sodium bicarbonate solution, water and a saturated brine solution. The organic phase was separated, dried over magnesium sulfate and concentrated to give 745 mg. of crude product which was purified by chromatographing on silica gel, 367 mg.

Workup

  1. additionTo a mixture of 710 mg
  2. additionwas added dropwise over a period of 15 minutes 574 mg
  3. stirringstirred overnight
  4. washthe organic layer washed successively with a saturated sodium bicarbonate solution, water
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 745 mg
  9. customof crude product which was purified by chromatographing on silica gel, 367 mg

Sources & evidence

ORD record
ord-ff6f4295e0c2409f841d353803a0f926
Source dataset
uspto-grants-1989_02
Patent number
US04808591

Reaction notes

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