Dichloromethane → HCID 178526724, compound

HRID 1199454Notes

Reaction equation

HRID 1199454 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]2[NH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].ClCCl.ClC1C=CC=C(C(OO)=[O:40])C=1>CO>[N+:1]([C:4]1[CH:28]=[CH:27][C:7]2[NH:8][C:9]([S:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:40])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 178526715HCID 178526715, compound

Product 1

HCID 178526724HCID 178526724, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the sulphide of step (a) above (1.15 mmoles) in methanol (70 ml)/dichloromethane (50 ml) was stirred at 10°. Solid m-chloroperbenzoic acid (80%; 1.38 mmoles) was added portionwise over 5 minutes. The solution was stirred at 10° for a further 30 minutes and then concentrated to approximately 25 ml. Silica gel (approximately 10 g) was added and the remaining solvent removed. Flash chromatography using dichloromethane containing 20 % ethyl acetate as eluant gave a pale orange solid (0.20 g) which was slurried in dichloromethane (50 ml) and filtered to give the title compound as an off-white solid, mp 208°-9° (dec).

Workup

  1. concentrationconcentrated to approximately 25 ml
  2. additionSilica gel (approximately 10 g) was added
  3. customthe remaining solvent removed

Sources & evidence

ORD record
ord-878f0ff2971c426ab98e7760aa8d9be1
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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