m-Chloroperbenzoic acid → HCID 15059546, compound

HRID 1199465Notes

Reaction equation

HRID 1199465 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][CH3:18].ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([CH3:18])=[O:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19866681HCID 19866681, compound

Product 1

HCID 15059546HCID 15059546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (b) above (2 g) was dissolved in dichloromethane (50 mls) and cooled to -10° with stirring. 85% m-chloroperbenzoic acid (1.6 g) was added portionwise. The reaction mixture was slowly warmed to room temperature and after 3 hours the reaction was complete. The reaction mixture was washed with aqueous metabisulphite solution, then bicarbonate solution and finally brine, dried over magnesium sulphate and evaporated to dryness in vacuo, then the residue was purified by flash chromatography (SiO2 /ethyl acetate 3:2 CH2Cl2) to afford the sub-title compound as a yellow crystalline solid, mp 157°-159°.

Workup

  1. temperaturecooled to -10°
  2. washThe reaction mixture was washed with aqueous metabisulphite solution
  3. dry with materialbicarbonate solution and finally brine, dried over magnesium sulphate
  4. customevaporated to dryness in vacuo
  5. customthe residue was purified by flash chromatography (SiO2 /ethyl acetate 3:2 CH2Cl2)

Sources & evidence

ORD record
ord-59787c4ffdd344bcb2a9140ae7fc99e7
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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