m-Chloroperbenzoic acid → HCID 14372495, compound

HRID 1723025Notes

Reaction equation

HRID 1723025 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2.C(=O)(O)[O-:19].[Na+].ClC1C=CC=C(C(OO)=O)C=1>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:19]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 14372494HCID 14372494, compound

Product 1

HCID 14372495HCID 14372495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5 ml. of tetrahydrofuran containing 170 mg. (0.71 mmol) of 8-(2-pyrimidylthio)quinoline was added 300 mg. of sodium bicarbonate and the mixture cooled to 0° C. m-Chloroperbenzoic acid (85%, 153 mg., 1.0 molar equivalent) in 5 ml. of the same solvent was added dropwise. After the addition was complete the reaction was allowed to warm to 25° C. and was stirred overnight. The reaction mixture was poured into a sodium bicarbonate solution and the product extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The residue was triturated with a small amount of ethyl acetate and filtered to yield title product, 84 mg., m.p. 152°-155° C.

Workup

  1. additionof the same solvent was added dropwise
  2. additionAfter the addition
  3. extractionthe product extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with a small amount of ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ef2f21f94b774b1787d7541356ece76b
Source dataset
uspto-grants-1989_08
Patent number
US04859679

Reaction notes

Loading…