m-Chloroperbenzoic acid → HCID 54494862, compound

HRID 482651Notes

Reaction equation

HRID 482651 reaction equation
[CH2:1]([C:4]1[C:5]([OH:29])=[C:6]([Cl:28])[C:7]([Cl:27])=[C:8]([CH:26]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([S:18]([N:21]=[CH:22][N:23]([CH3:25])[CH3:24])(=[O:20])=[O:19])[CH:12]=1)=[O:10])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl>[Cl:27][C:7]1[C:8]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([S:18]([N:21]=[CH:22][N:23]([CH3:24])[CH3:25])(=[O:19])=[O:20])[CH:12]=2)=[CH:26][C:4]2[CH2:1][CH:2]([CH2:3][OH:38])[O:29][C:5]=2[C:6]=1[Cl:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 54440926HCID 54440926, compound

Product 1

HCID 54494862HCID 54494862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

14.7 g (31 mmol) of 5-allyl-4-hydroxy-3'-dimethylaminomethyleneaminosulfonyl-2,3,4'-trichlorobenzophenone are suspended, with exclusion of moisture, in 60 ml of methylene chloride and, while cooling in an icebath, a solution of 7.4 g (43 mmol) of 90% pure metachloroperbenzoic acid in 60 ml of methylene chloride is added dropwise. The mixture is stirred for about one hour in the icebath and then briefly heated to 35° to 40° C., whereupon a clear solution is obtained. After allowing to stand at room temperature overnight, a further 0.7 g of metachloroperbenzoic acid is added, the mixture is stirred at room temperature for 4 hours and then again heated to 35° C. The precipitate is filtered off, washed twice with 10 ml of methylene chloride each time, and then washed several times with aqueous sodium bicarbonate solution until the reaction is alkaline. The organic phase is dried over sodium sulfate, the solvent is distilled off, and the amorphous product is purified by chromatography on silica gel using toluene/ethyl acetate (3:1 to 1:3). After distilling off the solvent and recrystallizing from a little methanol, colorless crystals of melting point 180°-182° C. are obtained.

Workup

  1. temperaturewhile cooling in an icebath
  2. temperaturebriefly heated to 35° to 40° C., whereupon a clear solution
  3. customis obtained
  4. waitto stand at room temperature overnight
  5. stirringthe mixture is stirred at room temperature for 4 hours
  6. filtrationThe precipitate is filtered off
  7. washwashed twice with 10 ml of methylene chloride each time
  8. washwashed several times with aqueous sodium bicarbonate solution until the reaction
  9. dry with materialThe organic phase is dried over sodium sulfate
  10. distillationthe solvent is distilled off
  11. customthe amorphous product is purified by chromatography on silica gel
  12. distillationAfter distilling off the solvent
  13. customrecrystallizing from a little methanol, colorless crystals of melting point 180°-182° C.
  14. customare obtained

Sources & evidence

ORD record
ord-0b7f6ece79e64680a9c5315645734959
Source dataset
uspto-grants-1986_03
Patent number
US04574128

Reaction notes

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