m-Chloroperbenzoic acid → HCID 178437431, compound

HRID 742330Notes

Reaction equation

HRID 742330 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:21]([S:27][CH3:28])[C:22]4[NH:26][N:25]=[N:24][N:23]=4)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:35])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>ClCCl>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:21]([S:27]([CH3:28])=[O:44])[C:22]4[NH:23][N:24]=[N:25][N:26]=4)=[CH:18][CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:35])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178437432HCID 178437432, compound

Product 1

HCID 178437431HCID 178437431, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.43 g (0.9 mmol) of the compound obtained in example 50 in 1.5 mL of dichloromethane, cooled to -78° C., was carefully added a solution of 0.27 g (0.81 mmol) of metachloroperbenzoic acid in 1.2 mL of dichloromethane. The cooling bath was removed, the reaction mixture was allowed to warm up to room temperature and was then heated at 30° C. for 90 min. Finally, it was allowed to cool to room temperature, water was added and it was extracted with dichloromethane. The organic phase was dried and the solvent was removed to afford a crude product that was chromatographed on silica gel (ethyl acetate-methanol-acetic acid mixtures of increasing polarity), to give the title compound of the example (yield: 37%).

Workup

  1. customThe cooling bath was removed
  2. temperaturewas then heated at 30° C. for 90 min
  3. temperatureto cool to room temperature
  4. additionwater was added
  5. extractionit was extracted with dichloromethane
  6. customThe organic phase was dried
  7. customthe solvent was removed
  8. customto afford a crude product that
  9. customwas chromatographed on silica gel (ethyl acetate-methanol-acetic acid mixtures of increasing polarity)

Sources & evidence

ORD record
ord-a8a6cc9756884ac3b98a0fd5e2d1d135
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

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