Dichloromethane → HCID 11482338, compound

HRID 355419Notes

Reaction equation

HRID 355419 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[OH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH3:28])[C:19]3[C:24]([S:25][C:26]=2[CH:27]=1)=[CH:23][CH:22]=[CH:21][CH:20]=3.ClCCl.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[OH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH3:28])[C:19]3[C:24]([S:25](=[O:9])[C:26]=2[CH:27]=1)=[CH:23][CH:22]=[CH:21][CH:20]=3

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 63853310H-phenothiazine-3-methanol, 10-methyl-

Product 1

HCID 11482338HCID 11482338, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

With ice-cooling, m-chloroperbenzoic acid (1.66 g, 9.6 mmol) was added to a mixture of 3-hydroxymethyl-10-methylphenothiazine (1.94 g, 8.0 mmol) and dichloromethane (30 ml), and the mixture was stirred for 1.5 hours and then at room temperature for 1.5 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the reaction product was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; methanol:chloroform=3:97 then 10:90) to give the title compound (1.95 g, 7.52 mmol, 94%) as colorless crystals.

Workup

  1. temperatureWith ice-cooling
  2. waitat room temperature for 1.5 hours
  3. extractionthe reaction product was extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-7d01e06b8cdb42789781689c819db878
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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