Chloroform → HCID 13913573, compound

HRID 330031Notes

Reaction equation

HRID 330031 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([S:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([S:27]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:36][CH:37]=1)=[O:9])[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 14098085HCID 14098085, compound

Product 1

HCID 13913573HCID 13913573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 ml of dry methylene chloride containing 304 mg of 3-chloroperbenzoic acid were added to 368 mg of methyl 4-[1-(2-methoxyphenyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 9) in 7 ml of dry methylene chloride, and the resulting mixture was stirred at 0°-5° C. for 30 minutes. At the end of this time, chloroform was added to the reaction mixture, and the resulting mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography eluted with a 10:1 volume mixture of ethyl acetate and methanol, to give 263 mg of the title compound as colorless crystals, melting at 113°-115° C.

Workup

  1. washthe resulting mixture was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. washeluted with a 10:1 volume mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-aabc12ead55640c59f9b673683c9db41
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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